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Holiday Rentals and Homes 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.
    1 / 13
    3 of 5 stars (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4.5 of 5 stars (3) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Contemporary home with private setting just 3/10 mile walk through a private neighborhood association path to Skaket Beach. Back yard overlooks an active cranberry bog! Near the Cape Cod Bike Trail and less than a mile to Rock Harbor fishing fleet. There are 3 decks and a fully screened porch with... View all property information
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    Orleans, Cape Cod 02653
    1 / 14
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Huge price reduction for the last remaining week left (Someone s cancellation is your good luck!). July 9th to 16th now $4000 from $4750. Rare opportunity to vacation in Nauset Heights right on the waterfront! Perfect Beach House for the beach loving family or couple. Walk out the door to one... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    6 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Nauset Heights! Classic Cape Cod beach house overlooking the Atlantic. Expansive great room with fieldstone fireplace, wrap around porch, and views from practically every room! FRIDAY to FRIDAY rental. Additional amenities include: room fans (5), lobster pot, cd, outdoor shower (private/hot... View all property information
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    Orleans, Cape Cod 02653
    1 / 16
    1 Bedroom, 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 / 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. Enjoy the spacious screened-in porch and all amenities. Additional amenities include: room fans, lobster pot, outdoor shower (private/hot water), heat, dehumidifier,... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    4 of 5 stars (1) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    5 Blueberry Island Road, Orleans, MA (ID# 18404) Bright and spacious home just a short distance to Cape Cod Bay and Skaket Beach! This wonderful home provides all amenities and has cathedral ceilings in the living, dining and kitchen areas. 3 Bedrooms (2 Queens, 2 Twins) and 2 Baths. A/C units in... View all property information
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    Orleans, Cape Cod 02653
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    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Charming modern waterfront cottage 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 fans in the main... 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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    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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    Orleans, Cape Cod 02653
    1 / 26
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    15 Mill Pond Road, East Orleans, MA ID# 18164 ~ Mill Pond Area Beautifully decorated home in the desirable Mill Pond area and with central air!. This comfortable home has an updated ktichen with new appliances, countertops, and flooring. Gorgeous Great Room with Cathedral Ceiling and "46 inch TV,... View all property information
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    Orleans, Cape Cod 02653
    1 / 16
    4 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Peeks of the Atlantic Ocean from this hilltop home in East Orleans! Full of Cape Cod charm with a screened/enclosed sunporch that overlooks an expansive yard. Enjoy your privacy with over an acre of land just waiting for kites, volleyball, soccer, croquet, or shoot some hoops in the basketball... View all property information
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    Orleans, Cape Cod 02653
    1 / 19
    4.5 of 5 stars (2) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    41 Chestnut Drive - Waterfont on Pleasant Bay! (ID# 18583) Spend your vacation on a bluff overlooking Pleasant Bay! For those nature lovers who like total privacy, this beach house provides access by path to a private beach that is wonderful for windsurfers and sailors. 4 air conditioned bedrooms-... View all property information
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    Orleans, Cape Cod 02653
    1 / 13
    3 Bedrooms, 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
    1 / 26
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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
    1 / 21
    5 of 5 stars (5) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Priscilla Landing is on the Nauset Estuary and has private pathways to the Atlantic. The first floor has 3 bedrooms. One room has Queen sized bed with a private bath. Second room as 2 twins also with a private bath. The Master suite has a King sized bed, Private Bath with walk-in shower and a... View all property information
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    Orleans, Cape Cod 02653
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Newly refurbished ranch located on a knoll not far from Eldredge Park. This lovely vacation home is fresh and bright, offering brand new furniture with cottage charm, all amenities, and a flat-screen TV. Enjoy the ease of one floor living, the spacious patio with gas & charcoal grills, and... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Waterfront
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    21 Manito Road, East Orleans (ID# 114251) ~ Overlooking Meetinghouse River Lovely waterfront home on Meetinghouse River. First floor includes open living / dining area, eat- in kitchen with stainless steel applainces, 3 bedrooms and 2 baths. Lower level has one bedroom with a queen bed, half bath,... View all property information
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    Orleans, Cape Cod 02653
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    1 / 11
    3 of 5 stars (2) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    8 Hofe Road, Orleans MA (ID# 18392) ~ Close to Skaket Beach and Bike Trail Quoted by a previous tenant this is the best rental for the money....! Spacious ranch minutes away from Skaket Beach and the Cape Cod Rail Trail! Sliders lead from the dining area to a large shaded deck which overlooks a... View all property information
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    Orleans, Cape Cod 02653
    1 / 7
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    This small two bedroom home has all the quiet charm that you would expect for your cape cod vacation. Perfect for a couple or a small family, this home offers relaxation. - All reservations have a $60 reservation fee and a refundable security deposit. - Additional amenities include: coffee maker,... View all property information
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    Orleans, Cape Cod
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Beautiful 2 bedroom home in the Tonset area of East Orleans with a great swimming area a mile down the street, a boat or kayak launch 3/10 of mile away, and only 2 miles to Nauset Beach or everything Main Street in Orleans has to offer. The home is situated on a corner lot with a large backyard and... 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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    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 / 16
    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 / 16
    3 of 5 stars (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    74 Keziahs Lane, Orleans, MA(.ID#92638) Waterfront home overlooking Meetinghouse River. This unique single level home offers 3 bedroom and 2 bathrooms, fully equipped kitchen, spacious living area, and picturesque grounds with waterviews of The River. Just a short distance to Kents Point and... View all property information
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    Orleans, Cape Cod 02653
    1 / 14
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    At this lovely Nauset Heights location you will be just 3/10ths of a mile to Nauset Beach & only apprx. 1000 ft. to great inlet waters for kayaking, fishing or paddle boarding. This nice cottage has A/C, WIFI, gas grill, outdoor shower, cable TV, outdoor deck with furniture, beach chairs, coffee... View all property information
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    Orleans, Cape Cod 02653
    1 / 13
    5 of 5 stars (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful and spacious vacation home located in one of the best spots in East Orleans. This home offers 4 bedrooms appointed with gorgeous bedding and 3 1/2 artistically tiled bathrooms. The entire home is decorated with a summer theme of the best that Crate and Barrel has to offer. You can relax... View all property information
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    Orleans, Cape Cod 02653
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    World famous Nauset Beach is short walk from your door and the Village of East Orleans is the same distance in the other direction. You will find this home very spacious with a living room with game table, family room that boasts cathedral ceilings, dining room, large kitchen and 1/2 bath on the... 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 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Expansive ranch located on 1.5 acres in the beautiful Barley Neck area of East Orleans. This gracious home features central air-conditioning and fans in each room, a very spacious living/dining room combination with wonderful built-ins, three bedrooms, two and a half baths and a bright sunroom that... View all property information
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    Orleans, Cape Cod 02653
    1 / 11
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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
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    Orleans, Cape Cod 02653
    1 / 12
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    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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    Orleans, Cape Cod 02653
    1 / 14
    3 Bedrooms, 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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    244 Tonset Road, East Orleans (ID#125800) Adorable cottage in East Orleans. *Special for the week of July 4th, $1650/week! This home has a screened porch overlooking the private back yard and is located in a nice neighborhood equidistant to Nauset and Skaket Beaches. 3 bedrooms, Master bath has... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Situated on five acres of woods, this home is quiet and secluded yet only minutes from beaches, bike path, restaurants and shops. Originally built in the 1700’s, the house has been completely restored and modernized and offers all the conveniences you need – completely supplied updated kitchen,... View all property information
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    Orleans, Cape Cod 02653
    1 / 18
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    *If you can't find the dates available that you are looking for, we also have a second studio you may be interested in. Send us an inquiry and we will try to help you find the dates you want.* Beach Rose is a studio in “Holly Tree Cottages” available by world-renowned Nauset Beach. It offers high... View all property information
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    Orleans, Cape Cod 02653
    1 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Adorable updated two bedroom cottage with a bright screened in porch, outdoor shower and A/C units. Located in the Pine Tree Cottage colony. The first bedroom has a full bedroom and the second has two twins and there is a full bathroom with a shower. This cottage is perfect for a family of four or... View all property information
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    Orleans, Cape Cod
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Porch
    • Washer
    • Grill
    • Patio
    • Internet Access
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    1800s Antique Victorian only 1 mile from the Beach! Front porch rockers and side deck overlook the beautiful yard and gardens. The living room, dining room and family/tv room are very welcoming on the main level. One bedroom with a Queen bed is also located downstairs. Three additional bedrooms... 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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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Spectacular Location! An outstanding waterfront spot offering exceptional privacy. Want to unplug? This simple, rustic cottage (no wifi, no TV) is on a peninsula surrounded by salt water and has views of Mill Pond. Launch your kayak or boat from its shore to access Nauset Inlet and to the beautiful... View all property information
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    Orleans, Cape Cod 02653
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    • Internet Access
    • Patio
    • Air Conditioning
    • Sauna
    • Satellite TV
    • Private Outdoor...
    • DVD Player
    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
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    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Parking
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Water views with dock access out to Meetinghouse pond and Little Pleasant Bay. Absolutely charming two bedroom cottage with water access. This home is part of a 4 building compound on a private yard that abutts private conservation land with views of the river leading to Pleasant Bay. Bring your... View all property information
    Location Information
    Orleans, Cape Cod 02643
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Satellite TV
    • Internet Access
    • Parking
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Skaket Beach at just 1000 ft!! This gorgeous Orleans vacation rental home is located in the perfect spot for you to enjoy Cape Cod. At this lovely home you will be just 2/10ths of a mile from beautiful private access to Skaket Beach in Orleans on Cape Cod Bay. This home is located on an old Cape... View all property information
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    Orleans, Cape Cod 02653
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Grill
    • Air Conditioning
    • Parking
    • DVD Player
    • Washer
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Skaket Beach at just 2/10ths of a mile, gorgeous marsh views and will be completely completely renovated & newly furnished for 2013! This rental home is perfect for the family. It has a lovely deck area with deck furniture to enjoy the stunning views, central a/c to keep you comfortable, 3... View all property information
    Location Information
    Orleans, Cape Cod 02753
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Patio
    • Waterfront
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Prestigious location within Quanset Harbor Club Association. Built on 1.3 acres and only 3 houses away from the community’s private beach on beautiful Pleasant Bay. This is the perfect property to enjoy all that Cape Cod has to offer. Home is newly furnished with a new gourmet kitchen with high... View all property information
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    Orleans, Cape Cod 02653
    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Private Outdoor...
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Grill
    • Washer
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This exceptional compound is one-of-a-kind with a Main House, Carriage House and private pool. The Main house has a restaurant quality kitchen which will bring out the Iron Chef in you. Ample seating in the dining area with separate bar. Entertaining is easy in the Living Room with HDTV and DVD,... View all property information
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    Orleans, Cape Cod 02653
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Parking
    • Private Outdoor...
    • Washer
    • Grill
    • Internet Access
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Lovely expansive home with pool and privacy near Crystal Lake and Kents Point.58 Keziahs Lane . Going fast last 2 weeks available 6/24 - 7/1 and 7/8 - 7/15 MAKE A RESERVATION!! "Fields Cove" is a lovely 6000+ sq ft expansive home enjoying privacy and enchanting water views out over the in-ground... 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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    • DVD Player
    • Air Conditioning
    • Grill
    • Parking
    • Internet Access
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Charming remodeled 1930s cottage! This home is located in the desirable and scenic Mill Pond area in Orleans with a well kept yard and wrap-around deck. House is very comfortable with single story living. Three bedrooms (brand new mattresses) and 1 and a half baths are located off the main... View all property information
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    Orleans, Cape Cod 02653
    1 / 26
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Satellite TV
    • Housekeeping...
    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Ocean Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful waterfront vacation home with 180 degree unobstructed views of the Frostfish Cove, The River, Jack Knife Point and the mouth Pleasant Bay. This vacation home is about light-filled rooms virtually all with a view of the water, kayaking, canoeing, sailing, fishing and more: a most unique,... 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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    • Washer
    • Outdoor Dining Area
    • Satellite TV
    • Grill
    • Wi-Fi
    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
    Location Information
    Orleans, Cape Cod 02653