Vacation Home Rentals By Owner In Orleans, MA

Showing 120 Of 255 Vacation Rentals

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

Bath

Sleeps

$954.42

/ Nightly

Private Vacation Home

Elegant Coastal Retreat with Ocean Views Near Mill Pond

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$954.42

/ Nightly

Private Vacation Home

Spacious Skaket Beach Retreat

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$959.09

/ Nightly

Private Vacation Home

Spacious pet-friendly home, close to Nauset & Skaket beaches and Orleans village

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$961.42

/ Nightly

Private Vacation Home

Private Access to Nauset Beach, Beach Pass Included

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$984.95

/ Nightly

Private Vacation Home

Beautiful Cape Cod Summer Home

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(32)

$989.59

/ Nightly

Private Vacation Home

Private Beach Access, Large House in the Woods

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(37)

$995.02

/ Nightly

Private Vacation Home

Luxurious Waterfront Home!

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$1014.78

/ Nightly

Private Vacation Home

3 Minute Walk to Nauset Beach

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$1014.89

/ Nightly

Private Vacation Home

Just Over Half Mile to Nauset Beach - Sleeps 10

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$1023.26

/ Nightly

Private Vacation Home

New Build in 2021, Overlooking Cape Cod Bay, Steps away from Fisher beach!

Truro, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(21)

$1026.85

/ Nightly

Private Vacation Home

August 2027 weeks now available!

Truro, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(65)

$1234.92

/ Nightly

Private Vacation Home

5 bedrooms ocean view estate overlooking cape cod bay

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(11)

$1188.95

/ Nightly

Private Vacation Home

Breathtaking Home In The Pochet Association of East Orleans With Private Pool

East Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$1206.88

/ Nightly

Private Vacation Home

Cape Cod retreat near Nauset Beach with pool oasis

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Very Good(1)

$1229.36

/ Nightly

Private Vacation Home

Private Waterfront Property with Water Access to Nauset Beach

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(8)

$1287.56

/ Nightly

Private Vacation Home

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

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(17)

$1297.06

/ Nightly

Private Vacation Home

Waterfront E Orleans! Panoramic views, Dock, Central heating, kayaks, go to the store

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(4)

$1175.88

/ Nightly

Private Vacation Home

Artist Retreat Views of Ocean

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(35)

$1252.77

/ Nightly

Private Vacation Home

Spacious home w/Heated Pool - Perfect for multiple families

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

Rent a place that suits your needs

Bed

Bath

Sleeps

Vacation Home Rentals By Owner In Orleans, MA

$934.14

$954.42

$954.42

$959.09

$961.42

$984.95

$989.59

$995.02

$1014.78

$1014.89

$1023.26

$1026.85

$1234.92

$1188.95

$1206.88

$1229.36

$1287.56

$1297.06

$1175.88

$1252.77

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