Home Vacation Home Rentals By Owner In Orleans, MA

Showing 160 Of 255 Vacation Rentals
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Exceptional(18)

$677.55

/ Nightly
Private Vacation Home

SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$678.52

/ Nightly
Private Vacation Home

4 Acre Private Estate on the Water

Orleans, Massachusetts, United States

Bed 6

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(1)

$683.73

/ Nightly
Private Vacation Home

Relaxing Cape Cod Hideaway with Modern Comforts

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$686.8

/ Nightly
Private Vacation Home

4BR Kenrick Woods Getaway

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(2)

$691.28

/ Nightly
Private Vacation Home

The Salteen House. Family Cape Escape • Dogs Welcome • Near Nauset & Skaket

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(2)

$691.73

/ Nightly
Private Vacation Home

Quiet home near Pilgrim Lake with deck, W/D, AC, games, & large yard

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 9

Sleeps
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Exceptional(1)

$692.81

/ Nightly
Private Vacation Home

Ocean Harbor Estates

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(1)

$693.85

/ Nightly
Private Vacation Home

3 Cottages, Walk to Nauset Beach!

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(2)

$695.86

/ Nightly
Private Vacation Home

New 2026 Stunning East Orleans Home Steps from the Shores of a Beautiful Nauset Inlet Beach

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

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(43)

$701.9

/ Nightly
Private Vacation Home

Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(5)

$702.01

/ Nightly
Private Vacation Home

5BR Luxe Retreat: Room to Spread out. Wine Bar, Hot Tub, Bikes, Game Room

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(26)

$703.82

/ Nightly
Private Vacation Home

Spacious Game Room Close to Nauset Beach!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
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$720.05

/ Nightly
Private Vacation Home

Family Fun: Huge Game Room, Outdoor Shower & Walk 2 Lake – 10 min to Ocean & Bay

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(25)

$726.14

/ Nightly
Private Vacation Home

West-facing pure waterfront home in Orleans, overlooking Arey's Pond

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(6)

$728.21

/ Nightly
Private Vacation Home

Orleans Cape Cod, 3BR, Fire Pit, Central AC, 8 Min to Nauset Beach, Sleeps 10

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(1)

$730.29

/ Nightly
Private Vacation Home

Coveside: Town Cove Waterfront

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(7)

$732.42

/ Nightly
Private Vacation Home

Pond-Front Home w/ Water Views!

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(7)

$735.98

/ Nightly
Private Vacation Home

Stunning Home with In-Ground Pool!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(4)

$737.69

/ Nightly
Private Vacation Home

Cozy home close to the beach with deck, porch, W/D, & foosball table

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 5

Bath

Sleep 8

Sleeps
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Exceptional(4)

$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(4)

$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(4)

$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(4)

$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(4)

$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(4)

$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(4)

$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(4)

$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(4)

$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(4)

$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