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Holiday Homes and Apartments Orleans, MA

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    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    WATERFRONT on Bakers Pond! Take the path from the patio to your private pondfront to enjoy swimming, fishing and kayaking on this lovely freshwater pond. Designed as an airy contemporary cabin on 3 levels-- all with sunset water views-- this home has beautiful pine panelling and hardwood fir floors... View all property information
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    Orleans, Cape Cod 02653
    1 / 31
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This Orleans property features stunning views of Robert's Cove from almost every room in the house. This custom built home has a casual floor plan that takes advantage of the serene waterfront setting, as well as comfortable furniture for relaxing. Enjoy the pathway around Robert's Cove or bring... View all property information
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    Orleans, Cape Cod
    1 / 7
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Comfortable 4 bedroom home located on a quiet dead end road just a short distance from Rock Harbor and the Cape Cod Rail Trail. For the 2017 season: two new bathrooms, hardwood flooring, water filtration system, Wifi Internet access 55inch TV, DVD . Updated photos to come! Also enjoy relaxing in... View all property information
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    Orleans, Cape Cod 02653
    1 / 23
    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    About this property
    This warm and inviting 6 bedroom, 4 bath home sprawls over 4 stories of comfortable rooms with spacious, open living areas and a private, fully fenced back yard. Perfectly located in South Orleans, the house is just minutes from the Lower Cape villages of Chatham, Brewster and Orleans. A beautiful... View all property information
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    Orleans, Cape Cod 02653
    1 / 30
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    2013 WATERFRONT HOME! Gorgeous 3-level contemporary home with 180 degree view of a beautiful 28-acre lake and conservation lands. With water views from every room, this dramatic home has 3 exterior decks and a private path to the pond only 75 feet away. Set on a cul-de-sac on a private lane, it is... View all property information
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    Orleans, Cape Cod 02653
    1 / 16
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Porch
    • Waterfront
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    About this property
    100 Yards from Water! Its hard to beat the location and value of this charming, well-appointed, 3 bedroom cottage on picturesque Nauset Heights with a short walk to both inland waterways and famous Nauset Beach. Set in a beautiful and relaxing setting - a perfect refuge. 3 Bedrooms. One Queen.... View all property information
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    Orleans, Cape Cod 02653
    4 of 5 bubbles Reviewed 8 September 2016
    This is the 3rd time we've rented this place. Comfortable, clean and close to the beach. A 10 minute walk to the outer end of Nauset, and minutes to the inlet. Nice little...
    5 of 5 bubbles Reviewed 21 May 2016
    My family of four (inc. two young children) loved the four nights we spent at this cottage. Nice, well-maintained property in a beautiful, quiet area and only 10 minutes walk to...
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    1 / 26
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Light and bright spacious beach house sitting on the edge of a marsh at the end of a sandy lane-- just 2/10ths of a mile from Skaket Beach! This wonderful spot offers panoramic marsh views with peeks out to the waters of Cape Cod Bay. The recently renovated main floor consists of a lovely kitchen... View all property information
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    Orleans, Cape Cod 02653
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    1 / 16
    4 of 5 bubbles (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Renovated ranch with semi-finished lower level walkout tucked up on a hill in the lovely Brick Hill area of East Orleans. This nice vacation home is fresh and bright offering newer furnishings and convenience to the East Orleans Village and Nauset Beach. Three bedrooms accommodate 6 guests, with... View all property information
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    Orleans, Cape Cod 02653
    4 of 5 bubbles Reviewed 20 August 2014
    What a great cottage rental! Location is perfect. Close to Nauset Beach yet tucked away from traffic. We felt safe and cozy. Rooms are spacious and tastefully decorated. Layout is...
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    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    New Listing! Bright and spacious ranch located on a wonderful, 1.2 acre level lot off a quiet lane the desirable Barley Neck area of East Orleans. With A/C units in the living area, loft and bedrooms, and brand new finishes and furnishings throughout! Two bedrooms are on the main floor, each with a... View all property information
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    Orleans, Cape Cod 02653
    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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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    Orleans, Cape Cod 02653
    1 / 40
    Studio, 3 Bathrooms, Sleeps 12 | Quick View
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    Newly remodeled historic home. Heated Pool, Central AC, Sleeps 12, Linens & Towels Included! Peak Summer Weekly Rates: $9,500 (Rents Saturday - Saturday during peak season) This beautiful 1920 Orleans home, newly remodeled and redecorated, exudes Cape Cod charm, retains its original historic... View all property information
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    Orleans, Cape Cod 02653
    1 / 16
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Incredible spot! Expansive Cape cottage on a bluff in Nauset Heights overlooking Nauset Inlet and the Atlantic with a newer upper level deck and a private stairway down to the beach. Casual Olde Cape Cod with pine panelling throughout. The main floor bedrooms consist of a large bedroom with double... View all property information
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    Orleans, Cape Cod 02653
    1 / 26
    6 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Cape Cod elegance describes this beautiful, expansive home which sits peacefully at the end of the cul-de-sac adjacent to a cranberry bog. Ideal for the larger gathering with its great room with soaring cathedral ceiling, gorgeous eat-in kitchen, spacious TV loft, screened porch, deck and patio.... View all property information
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    Orleans, Cape Cod 02653
    1 / 36
    Studio, 4 Bathrooms, Sleeps 9 | Quick View
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    Elevated ocean views, walk to Nauset Beach. Linens included. Peak Summer Weekly Rates: $4,500 - $5,200 (Rents Saturday to Saturday during peak season) This spacious East Orleans home is located just off Nauset Beach in the desirable Grand View neighborhood. This neighborhood is characterized by... View all property information
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    Orleans, Cape Cod 02653
    1 / 17
    8 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Bright, open and very charming home on a well maincured lot with spacious patio and yard. Close to fresh water swimming at Bakers Pond, or go hiking, biking, or swimming at nearby Nickerson State Park. Two bedrooms on the main floor plus lower level with 2 twins. New ductless AC, kitchen, sofas,... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    17 Blue Heron Way (ID# 121865) - Watefront on Namequoit River Summer 2017! Wonderful Waterfront compound with incredible views of the Namequoit River and direct access to Pleasant Bay. This property has plenty of room for the extended family with a main house and guest cottage together sleeping up... View all property information
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    Orleans, Cape Cod 02653
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    Adorable cottage located in a beautiful, quiet area about 3/10ths of a mile from Nauset Harbor. The cozy living/dining/kitchen area features a brand new kitchen, queen sofa bed and A/C unit. The bedroom has a king bed (easily converted into 2 twins) and an A/C unit. A separate laundry area has a... View all property information
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    Orleans, Cape Cod 02653
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    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Waterfront on Nauset Harbor! Classic Cape located on an incredible property overlooking the water and beyond. Enjoy the lovely living area with fieldstone fireplace, relaxing on the spacious deck or taking the path to the shore's edge. Current updates include new carpeting throughout house,... View all property information
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    Orleans, Cape Cod 02653
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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.... View all property information
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    Orleans, Cape Cod 02653
    1 / 21
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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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    Orleans, Cape Cod 02653
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Absolutely charming Cape located in the very desirable Briar Springs area of East Orleans. Situated on a very beautiful and spacious lot, this home is light and bright throughout, offers lovely furnishings and is meticulously kept evoking the feeling of a true vacation get-away. The first floor... View all property information
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    Orleans, Cape Cod 02653
    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This lovely Contemporary Cape sits on almost an acre of land only 2/10ths of a mile from the sandy shore of Bakers Pond and 3/10 mile from Nickerson State Park (in Brewster). Light and bright throughout, this custom home features an open floor plan, gleaming hardwood floors and full amenities--... View all property information
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    Orleans, Cape Cod 02653
    1 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 6
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Lovely Summer Rental in East Orleans. Approximently 0.5 miles from Nauset Beach. This apartment will sleep 4. One seperate bedroom with queen bed. Bathroom and shower. Murphy bed available.in sitting area. Comfortable sitting area with Direct TV, WiFi, washer and dryer, microwave among the... View all property information
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    Orleans, Cape Cod 02653
    5 of 5 bubbles Reviewed 28 August 2015
    Had a wonderful week with our family at this beautiful apartment. It is exactly like the photos! Clean, quiet and relaxing! Would definitely return! The owners live on the...
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    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 only... View all property information
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    Orleans, Cape Cod 02653
    1 / 21
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Designed to look like an illustration from a children’s fairytale, this gracious and comfortable vacation home promises a magical vacation any time of the year. Enter through lush gardens into a surprisingly spacious, fully air conditioned home designed with relaxation, convenience, and fun in... View all property information
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    Orleans, Cape Cod 02653
    1 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Location, Location! Popular duplex cottage very close to Skaket Beach on Cape Cod Bay. Simple and beachy, each side rents separately and has its own deck. Unit 2 (#429) with two bedrooms, has a new kitchen for the 2014 season. Unit 1 (#428) has three bedrooms. Both share the enclosed outdoor... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    NEW LISTING! Charm oozes throughout this absolutely adorable duplex condo with 180 degree water views of Town Cove. This lovely spot is in a quiet in-town location within walking distance of shops, restaurants, live theatre and baseball games! Two bedrooms, one with a queen and slider to deck; the... View all property information
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    Orleans, Cape Cod 02653
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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 A/C has been added for the summer 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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    Orleans, Cape Cod
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Nauset Heights! Absolutely lovely, newly built guest house located just under a half mile from the sandy shore of Nauset Beach on The Atlantic. Designed with the cozy character of a barn with the finer amenities of today. Beautifully detailed throughout with authentic wide pine floors, sliding barn... View all property information
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    Orleans, Cape Cod 02653
    1 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Salt waterfront home located in the Ocean Harbor Association in East Orleans. This newly-furnished home is set on over an acre of beautiful multi-level grounds with frontage and views of Little Cove. Enjoy kayaking right from your backyard, access to the association tennis courts or deepwater... View all property information
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    Orleans, Cape Cod 02653
    1 / 18
    7 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Orleans, Cape Cod 02653
    1 / 15
    8 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    With its great views of Cape Cod Bay across Namskaket Marsh from upper and lower decks, this charming and newly renovated home offers peace and privacy. Located on a cul-de-sac with a shady front yard, the house has skylights, sunlit rooms, an open loft with a sleep sofa and sliders to the decks... View all property information
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    Orleans, Cape Cod 02653
    1 / 31
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    Spacious Bay Side Orleans Waterfront Home Next to Skaket Beach PEAK SUMMER WEEKLY RATE: 8,500 (linens included) Situated between Skaket Beach and Rock Harbor, this magnificent home leaves nothing to be desired. Commanding views and direct access to private beach land compliment the seclusion and... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Newly renovated sprawling ranch home located in the beautiful Briar Springs area of East Orleans. The highlights of this lovely, bright and open home are its spacious great room with vaulted ceiling whichs leads out to a large deck, a separate living/dining area, new granite kitchen, master bedroom... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Chill out (now with central A/C!) and relax at this wonderful waterfront retreat located in Mayflower Point. This charming cottage offers wonderful views of Lonnie's Pond and Kent's Point and has its own path to Lonnie's River leading out to Pleasant Bay. Perfect for boating or kayaking. Many... View all property information
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    Orleans, Cape Cod 02653
    1 / 6
    8 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Clean, comfortable and cozy cottage overlooking Rock Harbor Marsh. Wonderful screened in porch for your evening pleasure. 2 Bedrooms, 1 Bath. 1 Double, 2 Twins Additional amenities include: outdoor shower (private/hot water), outdoor furniture, room fans, lobster pot, coffeemaker. View all property information
    Location Information
    Orleans, Cape Cod 02653
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Patio
    • Satellite TV
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    • Pet-friendly
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    • Smoking allowed
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    About this property
    Spend time in this classic waterfront getaway know as The "Boathouse" at "Topside". Enjoy water views from every room. You and your guests will feel like you are on your own private boat, sailing the blue water of Pleasant Bay. Swim directly from your steps leading into the water or spend the day... View all property information
    Location Information
    Orleans, Cape Cod
    1 / 19
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    20 Deerwood Lane, East Orleans, MA (ID# 120896) 2017 Season! Wonderful Home in East Orleans with central A/C. Walk to restaurants or Sundae School after a relaxing day at Nauset Beach. This dog friendly (with homeowner approval) home features lots of room with 4 bedrooms, hardwood floors... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Adorable cottage located in a wonderful East Orleans neighborhood near Mill Pond and Snow Shore Landing. The interior of this cottage is as cute as a button. Updates include new outdoor furniture, mattresses, and brand-new ductless AIR-CONDITIONING. Just steps away from Robert's Cove for great... View all property information
    Location Information
    Orleans, Cape Cod 02653
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    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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    Orleans, Cape Cod
    1 / 18
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Step back in time in this classic turn of the century cottage with views of Cape Cod Bay. Located on a wonderful property with an expansive yard, a screened-in porch and a path down to the sandy shore of Cape Cod Bay. Additional amenities include: beach chairs, crock pot, room fans, lobster pot,... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 9
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Location, Location! Popular duplex cottage very close to Skaket Beach on Cape Cod Bay. Simple and beachy, each side rents separately and has their own deck. Unit 1 has three bedrooms (#428); Unit 2 has two bedrooms (#429). Both share the enclosed outdoor shower. Brand new Central AC! Additional... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Recently renovated home tucked up on a knoll located in a very pleasant East Orleans neighborhood. The addition of a new second floor consists of two spacious bedrooms that look out to a scenic pond across the way and a nice bath. The rest of the home offers comfortable furnishings with all... View all property information
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    Orleans, Cape Cod 02653
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Smoking allowed
    • x
    About this property
    AT SKAKET BEACH! This charming renovated 1927 Cape has ample room for 6, a master bedroom with a vaulted ceiling and a private half-bath, plus a lovely wraparound porch with hammock. The sunny interior features newly-painted floors, comfy furnishings throughout and excellent amenities, including... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Cosy, welcoming home in South Eastham. Our traditional Cape Cod house features 4 bedrooms, 2 baths, and a fully finished basement with easy access to beaches, the Cape Cod Bike Trail, shopping and restaurants. Three bedrooms and the living room have window A/C units. We are on a quiet wooded lane,... View all property information
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    Orleans, Cape Cod
    1 / 32
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Grill
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Sweeping Bay Views, Privacy, Two Full Kitchens (Pets Considered) Peak Summer Weekly Rates: $4,300 - $4,500 (Rents Saturday - Saturday during peak season) This unique vacation home is nestled between Rock Harbor to the east and Skaket beach to the west. The home has its own private boardwalk across... View all property information
    Location Information
    Orleans, Cape Cod 02653