Home Vacation Home Rentals By Owner In Orleans, MA

Showing 255 Of 255 Vacation Rentals
Slider Thumb
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

Bed 8

Bed

Bath 7

Bath

Sleep 20

Sleeps
Slider Thumb

$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
Slider Thumb
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
Slider Thumb

$2126.55

/ Nightly
Private Vacation Home

Brilliantly updated 5 Bedroom

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 4

Bath

Sleep 12

Sleeps
Slider Thumb
Exceptional(25)

$2235.79

/ Nightly
Private Vacation Home

4 miles to Orleans beaches & close to town!

Orleans, Massachusetts, United States

Bed 6

Bed

Bath 3

Bath

Sleep 12

Sleeps
Slider Thumb

$2260.01

/ Nightly
Private Vacation Home

Briar Springs Pool/Spa Getaway

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(9)

$2283.18

/ Nightly
Private Vacation Home

Orleans Resort Style Living with Pool and Hot Tub

Orleans, Massachusetts, United States

Bed 6

Bed

Bath 4

Bath

Sleep 12

Sleeps
Slider Thumb
Exceptional(19)

$2322.82

/ Nightly
Private Vacation Home

The Meeting House: 023-O Private Orleans resort-style compound: heated pool/spa, fire pit & cabana

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
Slider Thumb
Exceptional(2)

$2561.06

/ Nightly
Private Vacation Home

Beachfront house with amazing views of the Atlantic Ocean and Nauset Inlet.

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
Slider Thumb
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
Slider Thumb
Exceptional(26)

$2778.08

/ Nightly
Private Vacation Home

Private Estate, heated pool, outdoor kitchen, 9 bedrooms, 9.5 baths, sleeps 20

East Orleans, Massachusetts, United States

Bed 9

Bed

Bath 9

Bath

Sleep 21

Sleeps
Slider Thumb
Exceptional(12)

$2912.92

/ Nightly
Private Vacation Home

New Saltwater Heated Pool & Hot Tub -Less than 5 Minutes from Nauset Beach!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(18)

$3137.08

/ Nightly
Private Vacation Home

Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

Orleans, Massachusetts, United States

Bed 7

Bed

Bath 2

Bath

Sleep 26

Sleeps
Slider Thumb
Exceptional(16)

$3567.11

/ Nightly
Private Vacation Home

Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24

Orleans, Massachusetts, United States

Bed 10

Bed

Bath 10

Bath

Sleep 24

Sleeps
Slider Thumb
Exceptional(1)

$7021.28

/ Nightly
Private Vacation Home

Luxury 6 Bedroom Home

Orleans, Massachusetts, United States

Bed 6

Bed

Bath 4

Bath

Sleep 14

Sleeps
map-loader

Home Rent a place that suits your needs

Private vacation home

Private vacation home

View 255 Private vacation home

Home Most popular vacation rentals in Orleans

Slider Thumb
Exceptional(1)

$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
Slider Thumb
Exceptional(1)

$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
Slider Thumb
Exceptional(1)

$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
Slider Thumb
Exceptional(1)

$573.31

/ Nightly
Private vacation home

Luxurious, Modern Walk to Water!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(1)

$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
Slider Thumb
Exceptional(1)

$565.29

/ Nightly
Private vacation home

Mid-Century Contemporary

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(1)

$562.23

/ Nightly
Cottage

Captain's Quarters by Nauset Beach

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(1)

$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
Slider Thumb
Exceptional(1)

$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
Slider Thumb
Exceptional(1)

$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