Vacation Home Rentals By Owner In Orleans, MA

Showing 240 Of 255 Vacation Rentals

Exceptional(35)

$1252.77

/ Nightly

Private Vacation Home

Spacious home w/Heated Pool - Perfect for multiple families

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(8)

$1287.56

/ Nightly

Private Vacation Home

Nauset Beach Retreat! Pool w/Spa & Gas Fire Pit

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(17)

$1297.06

/ Nightly

Private Vacation Home

Waterfront E Orleans! Panoramic views, Dock, Central heating, kayaks, go to the store

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(3)

$1300.72

/ Nightly

Private Vacation Home

One Particular Harbor - East Orleans Waterfront Vacation Haven, Sleeps 10

Orleans, Massachusetts, United States

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Bath

Sleeps

$1315.95

/ Nightly

Private Vacation Home

Private getaway by Skaket Beach

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(55)

$1364.25

/ Nightly

Private Vacation Home

Large, Charming Cape Cod Home Close To Orleans And Chatham Beaches

Orleans, Massachusetts, United States

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Bath

Sleeps

$1500.64

/ Nightly

Private Vacation Home

Waterfront Orleans Oasis with a Private Deep Water Dock

Orleans, Massachusetts, United States

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Bath

Exceptional(29)

$1535.35

/ Nightly

Private Vacation Home

3 Bicycles Provided! Cape Cod Cottage w/ Deck

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(3)

$1626.14

/ Nightly

Private Vacation Home

Tonset Manor: 232-O East Orleans Vacation Estate Includes Guest House, Heated Pool, Hot Tub

Orleans, Massachusetts, United States

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Bath

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Exceptional(28)

$1646.94

/ Nightly

Private Vacation Home

Enchanting Waterfront Summer Escape on Pleasant Bay

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(5)

$1692.33

/ Nightly

Private Vacation Home

Luxury home located 2 min walk from Skaket Beach. Sunny, spacious and private.

Orleans, Massachusetts, United States

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Bath

Sleeps

$1700.21

/ Nightly

Private Vacation Home

Oceanfront, Spectacular Views, Nauset Beach

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$1734.78

/ Nightly

Private Vacation Home

1 Minute Walk to Nauset Beach

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(9)

$1790.74

/ Nightly

Private Vacation Home

Piece of Paradise: 054-OL Magnificent Orleans Estate w/Pool, Tennis, Assoc. Beach on Pleasant Bay

Orleans, Massachusetts, United States

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Bath

Sleeps

$1812.07

/ Nightly

Private Vacation Home

Stunning Lakefront Estate with a Private Beach, Tennis Court, & Game Room!

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(15)

$1812.51

/ Nightly

Private Vacation Home

Fabulous Family CapeHouse, with Views, Beach & Dock! Gatherings Inside and Out!

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(13)

$1895.3

/ Nightly

Private Vacation Home

Large House w/ample space- steps from Skaket Beach, close to CCRT and downtown!

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(21)

$1896.76

/ Nightly

Private Vacation Home

Featured in Boston Globe- fully renovated cape w/ pool & modern barn pool house

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(14)

$1935.02

/ Nightly

Private Vacation Home

Spacious, Brand New Home - 5 bedroom 6 bath!

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$2041.07

/ Nightly

Private Vacation Home

Hydrangea Hideaway: 236-O Luxurious Orleans Estate w/Pool, Cabana, Game Room, and Stunning Finishes

Orleans, Massachusetts, United States

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Rent a place that suits your needs

Private vacation home

View 255 Private vacation home

Most popular vacation rentals in Orleans

Exceptional(2)

$531.87

/ Nightly

Private vacation home

Experience the charm of Orleans at Skaket Beach Life

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$579.12

/ Nightly

Private vacation home

3 Mi to Nauset Beach! Family Home w/ Private Yard

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$578.17

/ Nightly

Private vacation home

Skaket Beach Area Home Sleeps 8

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$573.31

/ Nightly

Private vacation home

Luxurious, Modern Walk to Water!

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$571.12

/ Nightly

Private vacation home

Spacious Home Ideally Located a 5 Minute Drive from Nauset Beach

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$565.29

/ Nightly

Private vacation home

Mid-Century Contemporary

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$562.23

/ Nightly

Cottage

Captain's Quarters by Nauset Beach

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$507.78

/ Nightly

Private vacation home

Rock Harbor Retreat: Perfect vacation home: Book Reservations for Summer 2027

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$499.97

/ Nightly

Private vacation home

Walk to Nauset Beach, Updated and Cozy!

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$502.34

/ Nightly

Private vacation home

Rock Harbor Hideaway

Orleans, Massachusetts, United States

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Bath

Sleeps

Vacation Home Rentals By Owner In Orleans, MA

$1252.77

$1287.56

$1297.06

$1300.72

$1315.95

$1364.25

$1500.64

$1535.35

$1626.14

$1646.94

$1692.33

$1700.21

$1734.78

$1790.74

$1812.07

$1812.51

$1895.3

$1896.76

$1935.02

$2041.07

Rent a place that suits your needs

Most popular vacation rentals in Orleans

$531.87

$579.12

$578.17

$573.31

$571.12

$565.29

$562.23

$507.78

$499.97

$502.34

Most Popular Cities in Massachusetts