Home Vacation Rentals By Owner In Orleans, MA

Showing 120 Of 283 Vacation Rentals
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Exceptional(23)

$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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$2071.18

/ Nightly
Private Vacation Home

New 2026 A Private, Luxurious Waterfront Oasis on Town Cove in Orleans

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(12)

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Private Vacation Home

Pleasant Orleans cottage with quick access to ocean side & bay side beaches.

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(1)

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Private Vacation Home

Peaceful and private vacation rental on the pond!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(10)

$487.33

/ Nightly
Private Vacation Home

Short drive to town and popular beaches!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$388.41

/ Nightly
Private Vacation Home

Easy Walk to Scenic Kent's Point in Beautiful Orleans, MA - Pet Friendly!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
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Exceptional(1)

$626.33

/ Nightly
Private Vacation Home

Short Kayak Ride to Nauset Beach

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(23)

$288.61

/ Nightly
Private Vacation Home

Bike to Nauset Beach or Walk to Mill Pond!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(4)

$433.22

/ Nightly
Private Vacation Home

Orleans Beach Retreat

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(15)

$255.8

/ Nightly
Condo

Lakefront retreat w/ deck, dock, sandy beach, 4 watercraft, <6 mins to 2 beaches

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(11)

$788.57

/ Nightly
Private Vacation Home

Beach & Golf Hub w/ All-Season Sunroom in Cape Cod

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 9

Sleeps
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Exceptional(10)

$330.19

/ Nightly
Apartment

Cozy 1 bedroom with fenced in yard, porch, close to the bay beach & bike trail.

Brewster, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$2126.55

/ Nightly
Private Vacation Home

Brilliantly updated 5 Bedroom

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(75)

$1154.47

/ Nightly
Private Vacation Home

La Bella Vita! Heated Pool, Walk to Ocean Beaches, Sleeps 12 in 6 rooms

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(1)

$2754.02

/ Nightly
Private Vacation Home

Pochet Point Estate 056-O: Pochet Estate with Nauset Beach Access, Pool & Panoramic Views

Orleans, Massachusetts, United States

Bed 7

Bed

Bath 7

Bath

Sleep 16

Sleeps
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Exceptional(1)

$467.99

/ Nightly
Private Vacation Home

Walk to Nauset Beach

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(8)

$1287.56

/ Nightly
Private Vacation Home

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

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(29)

$292.61

/ Nightly
Apartment

Spacious Orleans Apartment With Private Beach Access

Orleans, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(1)

$774.49

/ Nightly
Private Vacation Home

Capeside: 540-O Vintage Luxury in Orleans

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(6)

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Private Vacation Home

Charming Marsh View Home Near Rock Harbor (2286)

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Home Most popular vacation rentals in Orleans

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Exceptional(6)

$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(6)

$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(6)

$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(6)

$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(6)

$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(6)

$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(6)

$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(6)

$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(6)

$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(6)

$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