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Holiday Rentals in Orleans, MA

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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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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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    Orleans, Cape Cod
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    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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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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    Orleans, Cape Cod
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
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    Studio, 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
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    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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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 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
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    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 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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    1 / 18
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    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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    Studio, 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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    Studio, 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
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    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
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    Orleans, Cape Cod 02653
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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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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    Orleans, Cape Cod 02653
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Charming period home located only 2/10ths of a mile from gorgeous Nauset Beach on The Atlantic. Enjoy the sunny deck, comfortable furnishings, wonderful country kitchen and spacious backyard. Attached apartment also available for rent. Additional amenities include: room fans, lobster pot, cd,... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
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    Studio, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    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
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    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
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Orleans, Cape Cod 02653
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    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    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
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    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    Beach, Kayaks, SUPs on Pristine Orleans Lake! (Pets Considered) Please Note: This home rents Sunday to Sunday in peak summer months Peak Summer Weekly Rates: $4,600 - $4,900 Expansive Waterfront Home on Crystal Lake in the heart of Orleans. Crystal Lake is a pristine fresh water lake located close... 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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    About this property
    Beautiful and spacious vacation home perfect for the extended family- set on an acre-plus lot on a quiet cul-de-sac offering association access to Pilgrim Lake (just a short 1/2 mile walk through the neighborhood), along with saltwater access to Arey's Pond less than 1/4 mile away! This rambling... View all property information
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    Orleans, Cape Cod 02653
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    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    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
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    Studio, 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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    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    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 other has a... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 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
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    Studio, 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, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    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
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    Studio, 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
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Great privacy in East Orleans! Enjoy this lovely 3-bedroom, 2-bath contemporary saltbox offering a bright and open floor plan and updated furnishings. Front-to-back living room with fireplace and a great screened porch open onto a spacious wraparound deck. This great vacation spot is gracefully... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Lovely three bedroom contemporary Cape with an open floor plan located in a private cul de sac neighborhood. Features wireless internet, deck and private outdoor shower and is near the bike trail. Two bedrooms are on the first floor. One with a trundle bed and the other with two twins. Upstairs... View all property information
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    Orleans, Cape Cod
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    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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    Orleans, Cape Cod
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    Studio, 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
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    Studio, 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
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    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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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Spotless home in a lovely quiet setting near the bike path. There are two living spaces and a first floor laundry and half bath. The first floor bedroom has a queen size bed. On the second floor there are two bedrooms with a queen bed and two twin beds and a full bath. Large two level deck. There... View all property information
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    Orleans, Cape Cod
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    Studio, 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
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    Studio, 7 Bathrooms, Sleeps 10 | Quick View
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    Superb Pleasant Bay Views, from Large, Luxurious, Secluded Orleans Vacation Home. Peak Summer Weekly Rates: $5,750 - $6,250 (Rents Saturday to Saturday during peak season) Nestled in the woods of South Orleans on Pleasant Bay on 6.5 acres, this gorgeous home is a luxurious way to vacation on the... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    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
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    Orleans, Cape Cod 02653
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Very spacious and nicely appointed home with two living rooms perfect for the larger get-together. Located on a wooded lot close to Little Pleasant Bay and the Paw Wah Pond boat ramp. Enjoy the nice deck and all amenities, including a refurbished kitchen and new flat-screen TV-- plus CENTRAL A/C!... View all property information
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    Orleans, Cape Cod 02653
    1 / 15
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Washer
    • Satellite TV
    • Grill
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Charming modern waterfront cottage-- now with A/C!-- located in the exclusive Mayflower Point section of Orleans where the Namequoit River meets Little Pleasant Bay. The secluded area boasts scenic water views, quiet nights and sounds of birds. The living space has a new whole-house fan, ceiling... View all property information
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    Orleans, Cape Cod 02653
    1 / 11
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Patio
    • Satellite TV
    • Washer
    • DVD Player
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This charming and pristine contemporary ranch, nestled in a private wooded paradise-Mayflower Point, is minutes by foot to private salt and fresh water accesses for boating, swimming, or fishing. Launch a kayak at ''The River'', leading to Pleasant Bay and the outer beaches, or, if you prefer,... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 21
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Washer
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Orleans, Cape Cod 02653
    1 / 21
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    WATERFRONT COTTAGE! Nestled on two acres in Mayflower Point is this absolutely lovely, newly renovated cottage. Light and bright with cottage character throughout, painted exposed beams, skylights and glorious views out to Pleasant Bay. Take the path to the water to kayak or canoe, walk to... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 20
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • DVD Player
    • Grill
    • Wi-Fi
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    Orleans, Cape Cod 02653
    1 / 18
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Satellite TV
    • Grill
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    Amenities & Details
    • Satellite TV
    • Washer
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Orleans, Cape Cod 02653