Vacation Rentals By Owner In Orleans, MA

Showing 100 Of 283 Vacation Rentals

Exceptional(2)

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Private Vacation Home

Cheerful Home Close to Bay and Town

Orleans, Massachusetts, United States

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Sleeps

Exceptional(13)

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Private Vacation Home

Sprawling Home With Private Association Lake Access (2289)

Orleans, Massachusetts, United States

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Exceptional(8)

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Private Vacation Home

Spacious deck with amazing view, neighborhood path to Skaket Beach, game room

Orleans, Massachusetts, United States

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Exceptional(6)

$605.26

/ Nightly

Private Vacation Home

Steps to Skaket Beach!

Orleans, Massachusetts, United States

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Sleeps

Exceptional(1)

$876.12

/ Nightly

Private Vacation Home

Crystal Lake Waterfront Haven

Orleans, Massachusetts, United States

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Exceptional(69)

$2065.44

/ Nightly

Private Vacation Home

Luxury 8 Bedroom Home with Heated Pool - 4 minutes to the beach! Pet Friendly!

Orleans, Massachusetts, United States

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$448.76

/ Nightly

Private Vacation Home

Waterfront W/ AC & Magnificent View

Orleans, Massachusetts, United States

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$876.12

/ Nightly

Private Vacation Home

Crystal Lake Waterfront Cottage

Orleans, Massachusetts, United States

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Exceptional(17)

$842.47

/ Nightly

Private Vacation Home

100 Ft to Skaket Beach!

Orleans, Massachusetts, United States

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Exceptional(15)

$566.22

/ Nightly

Private Vacation Home

Private Path to Nauset Beach!

Orleans, Massachusetts, United States

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Sleeps

$520.09

/ Nightly

Private Vacation Home

Nauset Breeze - charming 2-bedroom house in beautiful Orleans with AC

Orleans, Massachusetts, United States

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Exceptional(11)

$457.04

/ Nightly

Private Vacation Home

Close to Nauset Beach!

Orleans, Massachusetts, United States

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Bath

Sleeps

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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Sleeps

Exceptional(1)

$730.29

/ Nightly

Private Vacation Home

Coveside: Town Cove Waterfront

Orleans, Massachusetts, United States

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Sleeps

$1014.78

/ Nightly

Private Vacation Home

3 Minute Walk to Nauset Beach

Orleans, Massachusetts, United States

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Sleeps

Exceptional(4)

$440.29

/ Nightly

Private Vacation Home

Pondfront, 1 Mile to Nauset Beach!

Orleans, Massachusetts, United States

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Sleeps

Exceptional(2)

$608.97

/ Nightly

Private Vacation Home

Long View Cottage Close to Nauset, Skaket, & Bakers Pond

Orleans, Massachusetts, United States

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Sleeps

Exceptional(11)

$1188.95

/ Nightly

Private Vacation Home

Breathtaking Home In The Pochet Association of East Orleans With Private Pool

East Orleans, Massachusetts, United States

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Sleeps

$589.54

/ Nightly

Private Vacation Home

Skaket Beach Area Home with Association Beach Access

Orleans, Massachusetts, United States

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Sleeps

Exceptional(2)

$578.17

/ Nightly

Private Vacation Home

Skaket Beach Area Home Sleeps 8

Orleans, Massachusetts, United States

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Rent a place that suits your needs

Private vacation home

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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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Sleeps

Exceptional(2)

$578.17

/ Nightly

Private vacation home

Skaket Beach Area Home Sleeps 8

Orleans, Massachusetts, United States

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Sleeps

Exceptional(2)

$573.31

/ Nightly

Private vacation home

Luxurious, Modern Walk to Water!

Orleans, Massachusetts, United States

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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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Vacation Rentals By Owner In Orleans, MA

$605.26

$876.12

$2065.44

$448.76

$876.12

$842.47

$566.22

$520.09

$457.04

$531.87

$730.29

$1014.78

$440.29

$608.97

$1188.95

$589.54

$578.17

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