Vacation Home Rentals By Owner In Orleans, MA

Showing 140 Of 255 Vacation Rentals

$589.54

/ Nightly

Private Vacation Home

Skaket Beach Area Home with Association Beach Access

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(14)

$598.25

/ Nightly

Private Vacation Home

Orleans Ranch Style Home Close to Town

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(13)

$599.31

/ Nightly

Private Vacation Home

Private Retreat on Pilgrim Lake! (1507)

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(15)

$599.74

/ Nightly

Private Vacation Home

Beach Getaway with Private Backyard!

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$604.52

/ Nightly

Private Vacation Home

Spacious and unique 4-bedroom house with private beach in marvelous Orleans

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(21)

$604.75

/ Nightly

Private Vacation Home

Two-story home with new kitchen, washer/dryer, large yard, and pool table

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$605.26

/ Nightly

Private Vacation Home

Steps to Skaket Beach!

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$608.97

/ Nightly

Private Vacation Home

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

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$622.03

/ Nightly

Private Vacation Home

Heated Plunge Pool, Theater Room, Backyard Fun!

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$626.33

/ Nightly

Private Vacation Home

Short Kayak Ride to Nauset Beach

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(13)

$634.68

/ Nightly

Private Vacation Home

Waterfront on Cape Cod Bay!

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(33)

$642.7

/ Nightly

Private Vacation Home

Private Beach and Roof Top Deck!

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(7)

$642.83

/ Nightly

Private Vacation Home

Charming 3-bedroom house with WiFi, Dogs considered, in Orleans

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$652.37

/ Nightly

Private Vacation Home

Walk to Rock Harbor Beach from your spacious Orleans coastal retreat

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(12)

$655.7

/ Nightly

Private Vacation Home

Spacious 5-Bedroom Retreat in the Heart of Orleans, MA

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$662.03

/ Nightly

Private Vacation Home

East Orleans Waterview Getaway

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$662.48

/ Nightly

Private Vacation Home

Waterfront Oasis with Game Space, Newly Renovated!

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(15)

$669.63

/ Nightly

Private Vacation Home

Beautifully remodeled cottage near the beach with central AC, gas grill & lawn

Orleans, Massachusetts, United States

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Bath

Sleeps

$676.59

/ Nightly

Private Vacation Home

Beautiful Historic Home Within a Mile of Crystal Lake

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(29)

$676.9

/ Nightly

Private Vacation Home

Beautifully Remodeled Classic Beach Home on Cape Cod Rail Trail

Orleans, Massachusetts, United States

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Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 255 Private vacation home

Most popular vacation rentals in Orleans

Exceptional(29)

$531.87

/ Nightly

Private vacation home

Experience the charm of Orleans at Skaket Beach Life

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$579.12

/ Nightly

Private vacation home

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

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$578.17

/ Nightly

Private vacation home

Skaket Beach Area Home Sleeps 8

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$573.31

/ Nightly

Private vacation home

Luxurious, Modern Walk to Water!

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(29)

$571.12

/ Nightly

Private vacation home

Spacious Home Ideally Located a 5 Minute Drive from Nauset Beach

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$565.29

/ Nightly

Private vacation home

Mid-Century Contemporary

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$562.23

/ Nightly

Cottage

Captain's Quarters by Nauset Beach

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$507.78

/ Nightly

Private vacation home

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

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$499.97

/ Nightly

Private vacation home

Walk to Nauset Beach, Updated and Cozy!

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$502.34

/ Nightly

Private vacation home

Rock Harbor Hideaway

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Vacation Home Rentals By Owner In Orleans, MA

$589.54

$598.25

$599.31

$599.74

$604.52

$604.75

$605.26

$608.97

$622.03

$626.33

$634.68

$642.7

$642.83

$652.37

$655.7

$662.03

$662.48

$669.63

$676.59

$676.9

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