Home Vacation Rentals By Owner In Orleans, MA

Showing 240 Of 283 Vacation Rentals
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Exceptional(3)

$440.03

/ Nightly
Private Vacation Home

Walk to Water, Cozy, Dog Friendly!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
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Exceptional(25)

$553.82

/ Nightly
Private Vacation Home

VACATION IN CAPE COD'S MOST BEAUTIFUL TOWN!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(17)

$815.46

/ Nightly
Private Vacation Home

4-bedroom Vacation Home Less Than 1 Mile to Nauset Beach, AC, Fire-Pit

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 9

Sleeps
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Exceptional(13)

$401.72

/ Nightly
Private Vacation Home

Steps to Rock Harbor, Fully Renovated Cape Cod Cottage

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(18)

$894.24

/ Nightly
Private Vacation Home

Cape Cod Sunscape. Orleans

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(21)

$1026.85

/ Nightly
Private Vacation Home

August 2027 weeks now available!

Truro, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(1)

$697.98

/ Nightly
Private Vacation Home

Classic Cape Beauty in East Orleans, close to Asa's Landing & Weesit Point

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(2)

$246.07

/ Nightly
Cottage

Wonderful 2-bedroom cottage with AC and Heat in charming Orleans, MA!

Orleans, Massachusetts, United States

Bed 2

Bed

Sleep 5

Sleeps
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Exceptional(10)

$513.72

/ Nightly
Cottage

Charming Restored Cottage near Nauset Beach, The Summer House

East Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(12)

$917.56

/ Nightly
Private Vacation Home

Comfortable, Cozy & Spacious Orleans Cottage on Quiet Road & Close to Everything

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 11

Sleeps
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$954.42

/ Nightly
Private Vacation Home

Elegant Coastal Retreat with Ocean Views Near Mill Pond

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$472.58

/ Nightly
Private Vacation Home

Nauset Heights Carriage House

Orleans, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(11)

$934.14

/ Nightly
Private Vacation Home

close to town and Nauset beach, EV charger, air conditioning, outdoor shower.

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Very Good(1)

$1229.36

/ Nightly
Private Vacation Home

Private Waterfront Property with Water Access to Nauset Beach

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(12)

$562.23

/ Nightly
Cottage

Captain's Quarters by Nauset Beach

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(3)

$662.03

/ Nightly
Private Vacation Home

East Orleans Waterview Getaway

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(4)

$502.34

/ Nightly
Private Vacation Home

Rock Harbor Hideaway

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(12)

$2092.96

/ Nightly
Private Vacation Home

A Wave From It All: 227-O Overlooks Nauset Beach/Atlantic, Heated Pool, Hot Tub & Fire-pit

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(37)

$424.94

/ Nightly
Private Vacation Home

Blue Sky Beach Bungalow East Orleans

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(3)

$1300.72

/ Nightly
Private Vacation Home

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

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Home Most popular vacation rentals in Orleans

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Exceptional(3)

$531.87

/ Nightly
Private vacation home

Experience the charm of Orleans at Skaket Beach Life

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(3)

$579.12

/ Nightly
Private vacation home

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

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(3)

$578.17

/ Nightly
Private vacation home

Skaket Beach Area Home Sleeps 8

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(3)

$573.31

/ Nightly
Private vacation home

Luxurious, Modern Walk to Water!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(3)

$571.12

/ Nightly
Private vacation home

Spacious Home Ideally Located a 5 Minute Drive from Nauset Beach

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(3)

$565.29

/ Nightly
Private vacation home

Mid-Century Contemporary

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

$562.23

/ Nightly
Cottage

Captain's Quarters by Nauset Beach

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(3)

$507.78

/ Nightly
Private vacation home

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

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

$499.97

/ Nightly
Private vacation home

Walk to Nauset Beach, Updated and Cozy!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

$502.34

/ Nightly
Private vacation home

Rock Harbor Hideaway

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps

Most Popular Cities in Massachusetts