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Orleans Luxury Holiday Homes

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177 rentals in Orleans.
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76 Barley Neck Road 20443
2 bedrooms
1 bathroom
Sleeps 4
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Landers Lane 18200
2 bedrooms
1 bathroom
Sleeps 4
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16 PRIMROSE LANE 123468
3 bedrooms
1 bathroom
Sleeps 7
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41 Pochet Rd 18558
2 bedrooms
1 bathroom
Sleeps 4
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Highly Rated Cottage in Orleans, Cape Cod
3 bedrooms
2 bathrooms
Sleeps 6
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East Orleans - walk to Nauset Beach
2 bedrooms
1 bathroom
Sleeps 4
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Walk to Crystal Lake; private Tennis Court; Basketball Hoop
5 bedrooms
5 bathrooms
Sleeps 10
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Luxury 7 BR, 4 BA w/ Unique 60 foot Private Pool, .4 Miles to Beach
7 bedrooms
4 bathrooms
Sleeps 21
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Quaint Cape Near Beaches And Centrally Located
3 bedrooms
2 bathrooms
Sleeps 6
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Unit #5 39659
1 bedroom
1 bathroom
Sleeps 4
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Save time - get the best Orleans rentals sent straight to your email!
Beautiful Orleans Pilgrim Lake Waterfront Home
4 bedrooms
4 bathrooms
Sleeps 10
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Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream
3 bedrooms
2 bathrooms
Sleeps 6
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CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE
2 bedrooms
3 bathrooms
Sleeps 8
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Booking now Summer 2021!
3 bedrooms
2 bathrooms
Sleeps 8
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Your perfect Cape Cod Getaway! Fully renovated cottage minutes from the beach!
2 bedrooms
1 bathroom
Sleeps 4
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Family home, 2 mi to Nauset Beach, sleep 8+, perfect for 2 families
4 bedrooms
3 bathrooms
Sleeps 10
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6 Twitchknot Farm Way 18018
1 bedroom
1 bathroom
Sleeps 2
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Enchanting Waterfront Escape on Pleasant Bay
4 bedrooms
5 bathrooms
Sleeps 7
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Your perch to the Cape's best ocean view with private Nauset access for 8!
4 bedrooms
3 bathrooms
Sleeps 8
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Walk to Skaket Beach
4 bedrooms
2 bathrooms
Sleeps 10
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Comfy studio cottage, walk to beach & dining - 300 yards to Nauset Beach!
0 bedrooms
1 bathroom
Sleeps 3
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Family-friendly, Colonial-style home complete w/ three-seasons patio & gas grill
4 bedrooms
2 bathrooms
Sleeps 8
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2 Greymoor Way 18282
4 bedrooms
4 bathrooms
Sleeps 8
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Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly
4 bedrooms
3 bathrooms
Sleeps 8
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14 Iyanough Road 80840
2 bedrooms
1 bathroom
Sleeps 4
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Waterfront,88 Tonset Road ID ***********
3 bedrooms
3 bathrooms
Sleeps 6
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29 Greymoor Way 18520
3 bedrooms
2 bathrooms
Sleeps 6
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Reserve your luxury vacation for 2021!
8 bedrooms
9 bathrooms
Sleeps 22
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Great cottage close to Nauset Beach; 040-O
3 bedrooms
2 bathrooms
Sleeps 6
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#519: Private beach access, Screened in dining, Wrap around porch! Dog friendly!
3 bedrooms
1 bathroom
Sleeps 6
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17 Center Place 18374
2 bedrooms
0 bathrooms
Sleeps 4
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12 Nauset Knolls Lane 71341
3 bedrooms
2 bathrooms
Sleeps 8
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Charming, Renovated 1870s Home with Private Beach
3 bedrooms
2 bathrooms
Sleeps 6
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4 miles to beaches & 1 mile to lakes! Family friendly, BBQ, A/C, full kitchen!
5 bedrooms
4 bathrooms
Sleeps 10
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#526: Luxury waterfront, private sunbathing beach. 9-seat movie theater - GAME R
6 bedrooms
4 bathrooms
Sleeps 14
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Main House 37244
4 bedrooms
2 bathrooms
Sleeps 8
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Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24
10 bedrooms
11 bathrooms
Sleeps 24
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Spacious Nauset Beach Home Sleeps 12+, 5 minute walk to beach, hot tub
5 bedrooms
5 bathrooms
Sleeps 14
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Spacious five BR only 5 min to Nauset Beach with convenient Pochet Inlet access
5 bedrooms
4 bathrooms
Sleeps 12
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Path to Skaket Beach
5 bedrooms
3 bathrooms
Sleeps 10
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6 Bayberry Way 18591
2 bedrooms
3 bathrooms
Sleeps 7
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Steps to Skaket Beach!
4 bedrooms
4 bathrooms
Sleeps 8
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Updated East Orleans 6 Bedroom Home with Heated Pool, linens incl. 004-O
6 bedrooms
4 bathrooms
Sleeps 12
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Cozy Cottage Overlooking Rock Harbor Creek
1 bedroom
1 bathroom
Sleeps 4
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48 Nauset Road 22262
4 bedrooms
3 bathrooms
Sleeps 8
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'Up There' 39452
2 bedrooms
3 bathrooms
Sleeps 6
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10 Cedar Land Road 40510
4 bedrooms
3 bathrooms
Sleeps 10
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97 Pochet Road 93127
4 bedrooms
2 bathrooms
Sleeps 8
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New listing! Stylish Orleans home w/ spacious deck - near bay & ocean beaches!
4 bedrooms
4 bathrooms
Sleeps 8
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On the Waterfront of Nauset Heights
3 bedrooms
2 bathrooms
Sleeps 6
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