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Holiday Rentals in Orleans, MA

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    Travellers to Orleans are booking May dates now. Secure your holiday rental today, and have the perfect trip.
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | 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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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Newly Listed and Newly Updated, this is the rental you’ve been looking for!! Situated in a secluded wooded neighborhood, not far from shops and restaurants. Perfect home base, just 1.7 miles from popular Skaket Beach on Cape Cod Bay, 1 mile from Rock Harbor sunsets, and the bike path is just .3... View all property information
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    Orleans, Cape Cod
    1 / 11
    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
    1 / 15
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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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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    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
    1 / 16
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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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
    Location Information
    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 20 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 / 7
    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, 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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    1 / 40
    Studio, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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, 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... 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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    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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    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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    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, 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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    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    • Waterfront
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    About this property
    20 Hayward Lane, East Orleans (ID# 108991) Close to Nauset Beach MeetingHouse Pond, Pleasant Bay and Village of East Orleans 2017 Season! Enjoy this lovely, large, sun-filled home in charming East Orleans on a spacious, 1.5 acre private property with saltwater views of Frostfish Cove (leading to... 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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    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 8 | Quick View
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    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
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    Orleans, Cape Cod 02653
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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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 association... 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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    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, 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 / 14
    5 of 5 bubbles (1) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Enjoy a beautiful setting at this Orleans vacation rental. There are 2 bedrooms, 1 bathroom, a lovely deck area and gorgeous landscaping. Within a quick drive to Nauset Beach, Orleans Village with restaurants and shops yet set in a quiet spot. There is Cable / Satellite TV, cooking / serving... View all property information
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    Orleans, Cape Cod 02653
    1 / 14
    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, 3 Bathrooms, Sleeps 6 | Quick View
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    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, 3 Bathrooms, Sleeps 9 | Quick View
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    21 Manito Road, East Orleans (ID# 114251) ~ Overlooking Meetinghouse River 2017 Season! Lovely waterfront home on Meetinghouse River. First floor includes open living / dining area, eat- in kitchen with stainless steel appliances, 3 bedrooms and 2 full baths. 1st Bedroom King Bed with slider to 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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    7 Mallard Drive, Orleans MA( ID# 49614) Close to Skaket Beach 2017 Season! Wonderful home near Skaket Beach, A/C, private yard, quiet neighborhood! Just under 1 mile to Skaket Beach from this beautiful 3 bedroom, 3 bath home on the bayside of Orleans! Spacious home with all of the desired... 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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    Nauset Beach!! At this lovely East Orleans vacation rental home you can enjoy the best of Cape Cod. This 4 bedroom, 2 bath home has everything you need for a comfortable stay here in East Orleans. There are A/C units, WIFI internet access,, outdoor grill and plenty of outdoor living space. The... View all property information
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    Orleans, Cape Cod 02653
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    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    27 Pond Road, Orleans (ID# 22347) 2017 Season! Nestled on a private 1.5-acre wooded lot, this charming and newly constructed home combine’s comfort with gracious living! The large kitchen features high-end appliances, marble counters, breakfast booth with bay windows and opens to the dining area... View all property information
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    Orleans, Cape Cod 02653
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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
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    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
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    Orleans, Cape Cod 02653
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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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    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
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    Studio, 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
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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, 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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    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
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    Studio, 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
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    Studio, 1 Bathroom, Sleeps 6 | 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 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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    • Pet-friendly
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    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Lovely 3 bedroom, 1.5 bath East Orleans Cottage located in a quiet and private area of East Orleans convenient to great waters for kayaking, paddle boarding, walking along the water edge and Nauset Beach. This cute cottage has WIFI, flat screen TV, nice deck and yard, outdoor shower, A/C, cooking /... 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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    • Patio
    • Air Conditioning
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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 8 | Quick View
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    • Internet Access
    • Satellite TV
    • Balcony
    • Waterfront
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Breathtaking views of Nauset Harbor and tucked away at the end of a private drive. With cathedral ceilings and lots of windows, this cottage offers spectacular waterviews from almost every room. The sun rises over the dunes and harbor right into both sitting rooms and dining area...sunset is even... View all property information
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    Orleans, Cape Cod 02653
    1 / 20
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Satellite TV
    • Air Conditioning
    • Grill
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    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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 / 18
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    • 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
    1 / 18
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Grill
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Skaket Beach at just 4/10ths of a mile! At this beautiful 4 bedroom / 2 bathroom Orleans Vacation Rental home you will be just in just the right spot! 1/2 a mile to the Cape Cod bike trail & a real quick drive to the village area of town. Located on a nice dead end road this lovely rental home... View all property information
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    Orleans, Cape Cod 02653
    1 / 8
    Studio, 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
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    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 / 13
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    • Air Conditioning
    • Parking
    • Internet Access
    • Patio
    • Grill
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    25 B Doane Road, East Orleans (ID# 106441) Nauset Heights 2017 Season! Adorable 2 bedroom cottage in Nauset Heights. Peeks of Mill Pond and around the corner from the landing. Cute, clean and charming 2 bedroom, 1 bath cottage with central air conditioning, part of the Pilgrim Lane cottages.... View all property information
    Location Information
    Orleans, Cape Cod 02653