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Holiday Homes and Apartments Orleans, MA

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    All 247 Rentals in Orleans
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    Travellers to Orleans are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    $1,014
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    1 / 11
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    $4,311
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    1 / 23
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    $1,395
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    1 / 9
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    1 / 19
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    Enjoy an expansive layout at this antique 3 bedroom, 3 full bath home featuring a living room, two dens, dining room, large open kitchen and much more! On the first level is a Master Suite with a queen sized bed and full bathroom, with a shower and large soaking tub. Just off the Master Suite is... View all property information
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    1 / 14
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This is a comfy, updated 2 bedroom cottage is nestled in a wooded area walking distance to Skaket Beach. With sleeping for 6 and 2 full bathrooms, this is a great rental for your vacation! The main living area is open and airy with a living, dining, kitchen area. The 2 main bedrooms are off this... View all property information
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    $2,409
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    1 / 44
    2 Bedrooms / 1 Bathroom / Sleeps 8
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    About this property
    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... View all property information
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    1 / 7
    Studio / 1 Bathroom / Sleeps 2
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    About this property
    Enjoy a nice private location with a large yard and extra garage for storage of bikes and beach items. This studio cottage offers a living room with a Full Sleeper Sofa and Cable TV, WIFI Internet & A/C. For your convenience there is a small kitchenette with a stove (no oven) and small apartment... View all property information
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    $1,141
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    1 / 17
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    Located beside Cedar Pond which is great for fishing, this home offers all of the privacy and convenience you could ask for while enjoying your Cape Cod vacation. Walk to Main Street and the Bike Trail in less than a half mile or bike to beautiful Skaket Beach - just a mile away! This home has a... View all property information
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    $1,522
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Set on a rise in a quiet South Orleans neighborhood, this single-level home offers plenty of privacy and living space: a living room opening to the backyard deck, a dining room, kitchen breakfast bar, and a family room leading to a sunroom that also opens to the backyard deck. Arey's Pond nature... View all property information
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    1 / 11
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    This delightful, newly renovated and furnished cottage is situated on 1.5 acres of land and offers peace and quiet - right on Pilgrim Lake in Orleans! Central Ac has been added for the 2014 season!!! This two bedroom, one bath cottage is perfect for a couple or small family of four. Take in the... View all property information
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    $1,775
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    1 / 14
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Convenient to Skaket Beach for saltwater activities, this home is also within walking distance to Baker’s Pond Landing for fresh water swimming and boating. The property features three bedrooms and two baths, sleeping 6 comfortably. The first level of the home features a kitchen, livingroom, dining... View all property information
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    1 / 31
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Delightful ranch located in the Nauset Heights area of East Orleans, just .2 miles away from Nauset Beach! The house is bright and cheerful with a nautical theme and features a deck offering peeks of the Atlantic Ocean. With four bedrooms and 2 baths, it sleeps 8 comfortably. The first floor... View all property information
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    1 / 11
    4 Bedrooms / 1 Bathroom / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Grill
    • Waterfront
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    About this property
    This classic Nauset Heights home sits directly on a bluff with magnificent views of Nauset Beach, the Atlantic Ocean, and Nauset Marsh. The cottage is a classic with great vintage details and has been updated with full interior painting, high end teak dining table, outdoor chairs, modern... View all property information
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    1 / 18
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Very convenient to everything Orleans has to offer, this well appointed home is just a short drive to Nauset Beach or town. This 4 bedroom, 2 bath home sleeps 8 comfortably, making it ideal for extended families. The property offers a nicely landscaped yard, deck, and patio as well as a gas grill... View all property information
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    1 / 10
    6 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Hot Tub
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    • Suitable for children
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    About this property
    Bring the whole family to this 6 bedroom, pet-friendly, East Orleans home that sleeps 12 and features an above garage apartment. This home is located at the end of a cul-de-sac about 1/2 mile away from Nauset Beach and boasts an open, expansive floor plan with a full kitchen, dining room, living... View all property information
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    1 / 16
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    This recently renovated 2 bedroom,1 bath cottage is nicely appointed in a prime East Orleans location, convenient to beaches and shopping. It is situated across the street from Town Cove and Asa's Landing and offers views of the water. The cottage has lovely grounds and gardens to enjoy, as well as... View all property information
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    1 / 25
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Smoking allowed
    • Suitable for children
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    About this property
    Built in 2013, this beautiful home abuts conservation land and sits at the end of a cul de sac offering great peace and quiet for your vacation. The interior is clean and nicely decorated and offers amenities like Wifi, cable tv and Central A/C, (central a/c also in lower level). The first floor... View all property information
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    1 / 14
    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    About this property
    This is a gorgeous contempory home with a path to your own private beach on Pleasant Bay. The house features 3 bedrooms that all have ensuite bathrooms and their own decks with waterviews. The lower level has 2 bedrooms each with 2 twins and the 2nd floor has a queen bedroom. The house sits on over... View all property information
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    $1,839
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    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This custom designed home was renovated just a couple years ago and is newly furnished and tastefully decorated. It has all the comforts and conveniences of home: bedroom A/C units on each floor; GenAir cook top with grill and griddle; double oven; gas & charcoal grills; 4 TVs, including new 36”... View all property information
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    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • Suitable for children
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    About this property
    This charming Cape sits on a large lot on a quiet street in Orleans. This is a great location with easy access to Skaket Beach, the Rail Trail for biking and also easy access to shops and restaurants. The deck overlooking a large yard is a great place to relax and unwind at the end of a busy day at... View all property information
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    $1,268
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    1 / 9
    Studio / 1 Bathroom / Sleeps 4
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    About this property
    This immaculate home is located in a quiet neighborhood within a 10 minute walk to Skaket Beach and a short distance away from the Cape Cod Rail Trail. The home offers a bright and breezy open floor plan with a living area featuring a futon for extra sleeping and a fully equipped kitchen. The home... View all property information
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    1 / 10
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Satellite TV
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    About this property
    Bright, clean and private best describe our home! When you first arrive at 'Nana's Place' you will not believe the manicured one acre lot. There is plenty of space in the front yard and back yard for kids to play. We even provide the toys (whiffle balls, kick balls, croquet, etc) And since our home... View all property information
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    $6,213
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    1 / 24
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Fireplace
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    About this property
    Steps to Skaket Beach this large 4BR/3BA home sits on a quiet sandy lane. Fully refurbished throughout with custom kitchen equipped with stainless steel appliances, custom antique white wood cabinetry, center island, granite counters and marble backsplash. All new luxury baths with stone/marble... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Newly renovated three bedroom two bath home close to the bike trail and 9/10th of a mile to picturesque Rock Harbor. Bright open kitchen/living room/dining area. Deck and great outside shower. Dishwasher, washer and dryer and central A/C. Large master bedroom has sky light and sitting area. One... View all property information
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    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Make yourself at home in this comfortable three bedroom Cape style home tucked away in a superb location, within walking distance to the center of town, public tennis courts, and the Orleans Fire Birds baseball games. Main level features a comfy living space open to dining area and leading to a... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    This lovely home sits in a peaceful, family-friendly neighborhood with a large landscaped front and back yard for family fun and games. With 4 bedrooms and 3 baths, it sleeps 8 very comfortably. The first level features a fully equipped kitchen, dining area, living room, and a bedroom with a queen... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    A very unique haven situated on what was a private family compound with private beach on Cape Cod Bay. The beach is less than 700 feet away via a beautiful sandy path which passes a cranberry bog along the way. The rambling, airy & bright 3000 sq. ft. home has been renovated over the past several... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Just a short distance to the center of Orleans, this well kept Saltbox style house is convenient to everything. It is only .3 miles to the bike path and 1.6 miles to Skaket Beach. The large grassy yard is private and spacious. The cute back deck comes equipped with an electric grill and outdoor... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    This beautiful 4 bedroom East Orleans home is just over a mile to popular Nauset Beach. The exterior of the home boasts a beautiful landscape and large, private driveway. The interior features a large and very open kitchen with beautiful hardwood floors and includes a dining area. Off the dining... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Antique home with Cape Cod charm. This cozy home offers great character throughout yet enjoys the desirable amenities of today. Originally constructed in the late 1800s, but updated in the late 1990s. The first floor consists of an open living room and dining area, airy kitchen, a bath with shower... View all property information
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    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    About this property
    Crystal Lake Waterfront! Enjoy fresh water swimming right outside your door! This wonderful, private spot is ideal for the extended family offering 5 bedrooms plus an office/den, including an incredibly spacious master bedroom suite and two other bedrooms that open out onto a screened porch that... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 9
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    • Gym
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    About this property
    Charming Cape Cod Antique in the Weeset area of East Orleans. There are many unusual and exciting elements to this rental. The owner is offering the use of a four-wheel drive vehicle to a two or more week reservation with access to both drive-on beaches at Nauset. The tenant must have sufficient... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    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 association... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    Nice contemporary home with open floor plan located on a natural wooded lot in a pleasant and peaceful neighborhood of South Orleans. Enter into a welcoming first floor that offers a wonderful open living room, dining area and kitchen, and full bathroom with shower and laundry. The second floor has... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Completely renovated, just like new, wonderful home on private cul-de-sac 3/4 of mile from Nauset Beach. Located right off Beach Road in lovely East Orleans. Upstairs has 2 large bedrooms, each with newer A/C units. One with 2 sets of bunks, each with a twin and full futon. Over sized full bath... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Bright, open and very spacious Cape centrally located on a cul-de-sac not far from Skaket Beach, Rock Harbor, The Cape Cod Rail Trail and Orleans Center. A wonderful, very well maintained home-- with a large deck ideal for eating summer meals or reading a book. Now with A/C units in the living room... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Suitable for children
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    About this property
    Pleasant Bay beach. (Private) is only a 3 minute walk away. Located on a private road, our unique, contemporary Cape Cod home offers a secluded setting, and lovely landscaping. The home is completely redecorated with a casually elegant Cape motif for your convenience and relaxation, including air... View all property information
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    5 Bedrooms / 4 Bathrooms / Sleeps 11
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    • x
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    About this property
    You will find that all your expectations are exceeded in this custom built Cape vacation dream home. The front door opens to an inviting and airy foyer complete with nautical décor and powder room. To the right you enter the large living room with ample seating and flat screen TV with DVD player.... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This vibrant and stylish 3BR/2BA classic home built in the 1800's is 6/10 mile to Skaket Beach. Pure old Cape Cod- perfect craftsmanship and the amenities we have all become accustomed to. The home is updated and in excellent condition but still retains much of its unique character and charm both... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    123 Areys Lane, Orleans -Property ID: 18226 Surrounded by serene woods, this inviting Cape has much to offer and is just 1/2 mile to Pilgrim Lake & 3 miles to Nauset Beach. This home features a sunny breezeway/ den that connects to a large eat-in kitchen, spacious living/ dining areas, three... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    Brand new renovation! Light and bright expansive ranch that has been beautifully and thoughtfully upgraded throughout. This architech-designed 'green' home is pristine and feels brand new! A few of its many highlights are its wonderful great room offering additional living space, inviting deck... View all property information
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    Studio / 1 Bathroom / Sleeps 3
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    About this property
    East Orleans Studio has it all. Take one of the deeded private paths to Nauset Beach from this couples getaway located at the end of a private road. The amenities for this spotless getaway include, a King size bed, Double size sleeper sofa (for an overnight guest), Full kitchen with D/W, Full bath... View all property information
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    1 Bedroom / 1 Bathroom / Sleeps 3
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    About this property
    1 bedroom - Queen size bed 1 bathroom - stall shower sofa bed - double size open living, dining & kitchen dishwasher refrigerator microwave 2 burner range top toaster oven coffee pot cable TV - DVD wireless internet AM-FM radio - disc player iron & board gas fireplace beach chairs &... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Waterfront
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    About this property
    Peaceful views and lake front living on Crystal Lake. 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 are currently under way including air conditioning, new hardwood floors, new windows,... View all property information
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    1 Bedroom / 1 Bathroom / Sleeps 3
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    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    • ?
    About this property
    Marsh Views Rock Harbor 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... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • ?
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    About this property
    Located in the desirable Captain Linnell area of Orleans, this home offers one floor living, a large yard, and is pet friendly! This lovely 3 bedroom, 1 bath home is just .3 miles to beautiful Skaket Beach and features cable TV, wireless internet and air conditioning! The Master Bedroom, just off... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • ?
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    About this property
    This classic Cape with wide-pine floors is located in a very quiet area just 8/10ths of a mile to Skaket Beach. The property features four bedrooms, two on the first level and two on the second, as well as a full bathroom on each floor. The two first floor bedrooms feature a queen sized bed and... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Suitable for children
    • x
    • x
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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' for the 2014 season including some new furniture, new rugs and curtains, and even a new flat... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Enjoy a serene setting with amazing views from this 3 bedroom Orleans home. Bring your kayaks & canoes to take full advantage of the lake front location. A private boat dock makes accessing the lake for swimming or boating easy. This home offers a nice open layout with views from almost every room... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    At the end of a private lane lies your secluded vacation retreat on tranquil Pilgrim Lake. Just 60 feet from the decks and living room window is your private lakefront with boat dock for swimming, boating or fishing. The main deck, overlooking the water with comfortable outdoor furniture and gas... View all property information
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