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Orleans Holiday Homes

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    Travellers to Orleans are booking July dates now. Secure your holiday rental today, and have the perfect trip.
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    Nauset Beach and Privacy1 / 12
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This 2 bedroom condo is equipped with kayaks and canoes right on the association dock. (First come first use with a few other condo units.) Renovations include air conditioning, new hardwood floors, new windows, outside shower, and additional half bath. The main level offers a fully stocked kitchen...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    New bedroom suite, recently expanded living room, flat screen TV's and 2nd full bath! This quaint 3 bedroom, 2 full bathroom Cape Cod Vacation Cottage is located on a spacious corner lot located just 3/10 of a mile from beautiful Skaket Beach in Orleans. Enter into cheerful living room, here you...
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    Orleans, Cape Cod 2653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    True Cape Cod Charm1 / 11
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 6 August 2017
    Located in Orleans which was in the middle of cape. Good restaurants and shopping. We loved the Christmas Tree Shop. It was easy to drive to other towns North or South. Flew...
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    About this property
    True Cape Cod Charm in every way! This 3 bedroom Saltbox is just up the road from Nauset Beach. All the upgraded conveniences you could want including granite counters, hardwood floors, washer/dryer, WIFI and 4 mini-split air conditioning units cool the entire home!. Relax in the outdoor shower or...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Charming remodeled 1930s cottage! This home is located in the desirable and scenic Mill Pond area in Orleans with a well kept yard and wrap-around deck. House is very comfortable with single story living. Three bedrooms (brand new mattresses) and 1 and a half baths are located off the main living...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cozy Cottage Overlooking Rock Harbor Creek1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Cozy Orleans bungalow with quintessential Cape Cod charm in historic Rock Harbor. Immaculately restored with granite counters and beautiful hardwood floors, tile bath, and high quality construction. Set within the tranquil beauty of Rock Harbor Creek and just 0.2 miles to Rock Harbor & Cape Cod...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Ideally located only a short stroll to Orleans Village and the Barley Neck Inn or a 10 minute bike ride to beautiful Nauset Beach, this newly renovated 2-bedroom is fully equipped for your total relaxation and enjoyment. Nestled among two acres of secluded woods and wetlands, 'Teal Pond' is located...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Rock Harbor Getaway1 / 16
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    Reviewed 1 week ago
    We have stayed here many times and have found the feel of home. The house is perfect for families or just an intimate getaway. Walking distance to the most glorious beach...
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    About this property
    Perfect house for family vacations and weekend getaways! Perfect location in the town of Orleans, Cape Cod. Walking distance to town as well as the Harbor. Less than 2 miles to Skaket Beach and 6 miles to Nauset Beach. Full amenities, washer, dryer, dishwasher. Nicely decorated and has a cozy...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Well appointed, comfortable, vacation home with central air, a deck, nice yard and within walking distance to beautiful Skaket Beach. Master bedroom has one queen size bed and the two other bedrooms have 2 single beds each. Full bathroom upstairs, half bathroom on first floor and an outdoor shower....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Charming Antique home with 6 bedrooms plus a den providing accommodations for up to 10 guests. Two kitchens, two living rooms, set on a huge lot in the lovely Barley Neck area of East Orleans. All the beds are new, it has been freshly painted and has a great yard. The barn has 2 miniature goats...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Enjoy the comfort of this conveniently located and well-appointed newer home. Nauset Beach (oceanside) with full amenities (restrooms, outdoor showers, Liam's for seafood, burgers, ice cream and more) is just a short drive (3.5 mi) from the house. Skaket Beach on the Cape Cod Bay with its long...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Spectacular Location! An outstanding waterfront spot offering exceptional privacy. Want to unplug? This simple, rustic cottage (no wifi, no TV) is on a peninsula surrounded by salt water and has views of Mill Pond. Launch your kayak or boat from its shore to access Nauset Inlet and to the beautiful...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Peeks of the Atlantic1 / 16
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Peeks of the Atlantic Ocean from this hilltop home in East Orleans! Full of Cape Cod charm with a screened/enclosed sun porch that overlooks an expansive yard. Enjoy your privacy with over an acre of land just waiting for kites, volleyball, soccer, croquet, or shoot some hoops in the basketball...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Wonderful home in very private East Orleans setting! Screened-in porch off the well-equipped kitchen area to enjoy all our summer meals. There is even a large deck off kitchen for grilling and relaxing. There are (3) bedrooms on first level including (1) king bedroom suite, and also (2) Queens size...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    Newly decorated, charming East Orleans escape just a mile and a quarter to fabulous Nauset Beach on The Atlantic. This sweet two bedroom home is located on a cul de sac convenient to East Orleans Village. Enjoy grilling on the patio with family and friends and the outdoor shower to wash all that...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Classic Cape1 / 14
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2014
    From the moment we drove up the driveway to the time when we finally left, our girls weekend was spectacular! This house that we rented was all we expected and more! Spacious...
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    About this property
    Classic Cape with bright, modern, free-flowing interior and central air conditioning in a tiny neighborhood on a private road in the woods (but only 2 miles to local stores). Private access to secluded salt-water beach on shallow bay, great for kayaking and beach-combing. Two master suites with...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    A Private Sunny Gem1 / 14
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    This private gem sits at the end of a sandy lane wrapped in trees and bathed in sunlight. The front deck welcomes you to sit and relax and enjoy the peace and quiet and plan your next days adventure. Located less the 2 miles from Nauset Beach and slightly farther from Cape Cod Bay, this Cape...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Walk to Baker's Pond to swim, kayak or paddle board. 5 bedroom, 3 bath home, plus an outdoor shower makes this home a great spot for families that like to vacation together. Gas grill on the deck along with outdoor seating to continue to enjoy the outdoors after a day at the beach. Main living area...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Deeded access to Crystal Lake, central A/C, water views This brand new luxury 3 bedroom home with central AC sleeps 8. It is a state of the art home built in 2014 with views of Crystal Lake in Orleans. Direct deeded access to Crystal lake comes with the home through short path down from the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Walk to Nauset Beach from this wonderful home. Once part of the historic Mayo Duck Farm and a 2/10 mile walk from beautiful Nauset Beach and the Atlantic Ocean. This home has been completely 'refreshed' including some new furniture, new rugs and curtains, and even a new flat screen television!...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Bike to Ocean and Bay beaches from this Orleans vacation home. Beautiful 3 bedroom, 1 bathroom, plus Outdoor Shower. Ranch style home. This home is a peaceful and charming property offering quick access to all of Cape Cods charm and activities. The open floor plan is perfect for entertaining with a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Overlooking the salt waters of Mill Pond and located in grand Ocean Harbor Estates! The Atlantic Ocean is just beyond this amazing waterway. Only 2 miles from Nauset Beach and 1.5 miles to East Orleans Village. This property has it all. Views, association dock and tennis court privileges. Open...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Recently renovated, spacious two-bedroom home with CENTRAL AIR-CONDITIONING sleeping six tucked up on a wooded knoll at Bakers Pond. This spot offers much privacy and is less than .1 mile to beautiful freshwater swimming and kayaking on the pond. This location feels removed from it all, yet is...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    ID#134634,14 Linda s Lane, Orleans 2018 Season! Great location not far away Nauset Harbor, Nauset Beach the Atlantic Ocean and Skaket Beach on Cape Cod Bay watch the sun set over the cape! Located on Lindas lane last house on the left very private yard home sitting on the hill side. Home offers an...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Waterfront 4 Bedroom on Crystal Lake in Orleans. This well appointed 4 bedroom has recently been fully updated. It has central AC throughout the home and it is quite spacious! Upper and lower floors all have lake front views. The main level has an eat in kitchen with mini bar with seating for 4....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Ocean Harbor Estates1 / 34
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Beautiful 4 bedroom home located in Ocean Harbor Estates that offers tennis, footpath to saltwater beach and boating access to Nauset Harbor and the Atlantic from Little Cove. A traditional Cape set up on a hill with a private back yard bordering a protected bird sanctuary. This home features 4...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    'Rose Cottage' is an absolutely lovely, light and bright expanded cottage located on almost an acre in the desirable Snow Shore area of East Orleans. Recently renovated with two bedroom suites (one on each level), separate sitting/sleeping alcove, multiple decks, and skylights. This wonderful...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Newly renovated ranch located on a cul-de-sac in the desirable Brick Hill area of East Orleans. Fresh, bright and open with Central Air Conditioning! Enjoy the newer furnishings throughout and all amenities. A great spot convenient to the sandy shore of Nauset Beach and The East Orleans Village.
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Freshwater Lakefront! Wonderful, newly renovated cottage set on 1.5 acres on Pilgrim Lake! Bright and open with cathedral ceilings, large fireplace and walls of glass overlooking the lake. This great spot offers much privacy with access to the fresh water out your back door, along with...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    15 Mill Pond Road, East Orleans, MA ID# 18164 ~ Mill Pond Area 2018 Season! Beautifully decorated home in the desirable Mill Pond area and with central air!. This comfortable home has an updated ktichen with new appliances, countertops, and flooring. Gorgeous Great Room with Cathedral Ceiling and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lovely Cape Cod Vacation Bungalow located in Orleans. The perfect Cape retreat near Skaket Beach and less than .5 mile to Orleans Town Center and Rock Harbor Beach! The bright, nautical-themed living room features a flat screen TV, DVD player, and a sleeper sofa. The kitchen if fully equipped with...
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    Orleans, Cape Cod 2653
    Cabin Holiday Rental - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Panoramic Views of the Atlantic1 / 26
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    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Reviewed 10 November 2016
    The house is designed perfectly for a couple of families who want to rent a beach house for a week or two. It is not only well-designed and practical, but is also spotless and...
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    About this property
    Priscilla Landing is on the Nauset Estuary and has private pathways to the Atlantic. The first floor has 3 bedrooms. One room has Queen sized bed with a private bath. Second room as 2 twins also with a private bath. The Master suite has a King sized bed, Private Bath with walk-in shower and a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    About this property
    This exceptional compound is one-of-a-kind with a Main House, Carriage House and private pool. The Main house has a restaurant quality kitchen which will bring out the Iron Chef in you. Ample seating in the dining area with separate bar. Entertaining is easy in the Living Room with HDTV and DVD, it...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    This 3 bedroom Cape Cod charm is bright and airy. This beautiful summer home is appointed with your comfort in mind and decorated with your love of Cape Cod at heart. Simple luxuries include hardwood floors, flat screen TV, DVD, Ping Pong Table and window A/C units in all of the bedrooms to keep...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Beautiful 4 bedroom home on private cul de sac in East Orleans. Pristine landscaped yard with swing set and hammock. Big kitchen that opens to the family room. Open den with tv and couches. Full bath, washer & dryer on the first floor. Upstairs has 3 large bedrooms with high ceilings and lots of...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Rare Blend of Classic Charm and Spacious Modern Upscale Accommodations, Sleeps 10 Peak Summer Weekly Rates:  $5,900-$7,200 Rents Saturday to Saturday in Peak Season Linens Included & Pets Considered NEW Listing for 2018! Originally built in 1800 with a recent addition, this historic property's...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Three bedroom with A/C * Wireless Internet * NO Pets Accepted 2018 Season! Located on a quiet street in a private setting this 3 bedroom, 3 bath tri-level home is just 1/2 mile to Rock Harbor & a short drive to Skaket Beach and the local shops and restaurants in Orleans! There is an AC unit in...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Completely renovated, absolutely gorgeous, Sea Captain's home located on over an acre in the highly sought after Nauset Heights area of East Orleans. Enjoy the light and breezy feeling throughout, the wonderful screened-in porch and the spacious deck with peeks of the ocean. A wonderful vacation...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Skaket Beach at just 1000 ft!! This gorgeous Orleans vacation rental home is located in the perfect spot for you to enjoy Cape Cod. At this lovely home you will be just 2/10ths of a mile from beautiful private access to Skaket Beach in Orleans on Cape Cod Bay. This home is located on an old Cape...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Nice 2 bedroom, 1.5 bath home so close you can WALK to your own private association beach on PLEASANT BAY. When you walk in the front door you go up a few stairs to get to the main level. The first level has a nice living room/dining room, a galley kitchen, and a relaxing 3 SEASON ROOM where you...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    NEW LISTING! Cozy, classic Cape Cod pine paneled cottage in 6-acre Nauset Farms Condominiums. Brand new ductless A/C, flat screen TV and sofa. A great location close to the East Orleans village and 3/4 of a mile from gorgeous Nauset Beach.
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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