Best price vacation rentals in Orleans, MA, USA • 150 Listings
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Orleans, MA, USA Vacation Rentals | 

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United States Massachusetts Chatham vacation rental compare prices direct by owner 26571076
5.0 (16)
201 Main Street Chatham - Sandpiper
Up to 8 guests
Airbnb$952
Vrbo$1,409
Booking.com$1,595
Average Nightly Rate
United States Massachusetts Wellfleet vacation rental compare prices direct by owner 33475681
Property Manager
5.0 (2)
Private, beautifully renovated home - walk to Wellfleet Cinemas & Rail Trail
Up to 6 guests
Vrbo$594
Property Manager
Airbnb
Booking.com
Average Nightly Rate
United States Tennessee Dennis vacation rental compare prices direct by owner 13084858
4.5 (1)
Straight Down to Inman Rd Beach
Up to 7 guests
Booking.com
Airbnb
Vrbo
United States Massachusetts Dennis Port vacation rental compare prices direct by owner 2658431
Property Manager
3.4 (20)
Summer Get Away
Up to 6 guests
Booking.com$134
Vrbo$231
Property Manager
Airbnb
Average Nightly Rate
United States Massachusetts Chatham vacation rental compare prices direct by owner 194137
5.0 (19)
Charming Chatham Cottage!
Up to 8 guests
Vrbo$719
Airbnb
Average Nightly Rate
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United States Massachusetts Chatham vacation rental compare prices direct by owner 274475
5.0 (5)
Ocean views Walk to Beach Pet Friendly AC Private
Up to 10 guests
Vrbo$640
Booking.com
Average Nightly Rate
United States Massachusetts Chatham vacation rental compare prices direct by owner 1984235
5.0 (1)
Newly updated home sleeps 7, AC, free WIFI, half mile to town
Up to 7 guests
Vrbo$503
Booking.com
Average Nightly Rate

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United States Massachusetts Orleans vacation rental compare prices direct by owner 2617680
5.0 (1)
Bayberry House - 5 minute drive to Nauset Beach
Up to 6 guests
Vrbo$257
Airbnb
Average Nightly Rate
United States Massachusetts Eastham vacation rental compare prices direct by owner 2642041
5.0 (1)
Dog Friendly 4 Bedroom with Pool, Walk to Beach
Up to 9 guests
Vrbo$844
Airbnb
Average Nightly Rate

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United States Massachusetts Harwich vacation rental compare prices direct by owner 11713992
5.0 (9)
Abigail Adams Home
Up to 8 guests
Vrbo$364
Airbnb
Average Nightly Rate
United States Massachusetts Eastham vacation rental compare prices direct by owner 13078381
5.0 (13)
EASTHAM 3 bedroom getaway near National Seashore
Up to 6 guests
Vrbo$358
Airbnb
Average Nightly Rate
United States Massachusetts Chatham vacation rental compare prices direct by owner 23652174
5.0 (32)
Sunny Updated Chatham Village 2 Bedroom Condo W/ Large Private Deck
Up to 5 guests
Vrbo$412
Airbnb
Average Nightly Rate
United States Massachusetts Harwich Port vacation rental compare prices direct by owner 25162252
5.0 (5)
6 Brooks Lane Harwich Port Cape Cod- - Brooks Lane Beach House
Up to 10 guests
Vrbo$511
Booking.com
Average Nightly Rate
United States Massachusetts Brewster vacation rental compare prices direct by owner 26603635
5.0 (21)
Brewster Ocean Edge Condo, Easy Breezy Fun!
Up to 4 guests
Vrbo$202
Airbnb
Average Nightly Rate
United States Massachusetts Orleans vacation rental compare prices direct by owner 29886201
5.0 (1)
Dogwood - Dog Friendly 3 Bedroom Near Nauset Beach
Up to 6 guests
Vrbo$560
Airbnb
Average Nightly Rate
United States Massachusetts West Harwich vacation rental compare prices direct by owner 33317316
5.0 (1)
Beach Plum Cottage - Dog-friendly, neighborhood beach, deck, sunroom, patio! ...
Up to 8 guests
Vrbo$520
Booking.com
Average Nightly Rate
United States Massachusetts Chatham vacation rental compare prices direct by owner 26606548
5.0 (58)
Now Open for Fall 2025 | Dog Friendly Home!
Up to 8 guests
Vrbo$508
Airbnb
Average Nightly Rate
United States Massachusetts Eastham vacation rental compare prices direct by owner 227738
5.0 (53)
Home On Minister Pond
Up to 8 guests
Vrbo$359
Airbnb
Average Nightly Rate
United States Massachusetts Chatham vacation rental compare prices direct by owner 11441948
5.0 (102)
Moongazer, Newly renovated, Family gathering place
Up to 8 guests
Vrbo$1,555
Airbnb
Average Nightly Rate
United States Massachusetts Chatham vacation rental compare prices direct by owner 235293
4.9 (113)
Chatham, MA - 6 Sabins Lane 5BR + Outdoor Shower
Up to 10 guests
Vrbo$359
Airbnb
Average Nightly Rate
United States Massachusetts Chatham vacation rental compare prices direct by owner 185282
4.9 (79)
Main Street Chatham Village Downtown-New Listing!
Up to 6 guests
Vrbo$351
Airbnb
Average Nightly Rate
United States Massachusetts Chatham vacation rental compare prices direct by owner 524616
4.9 (12)
Walk to Beach Heated Pool Pet Friendly AC WiFi Sand Simeon
Up to 14 guests
Vrbo$1,643
Booking.com
Average Nightly Rate
United States Massachusetts Chatham vacation rental compare prices direct by owner 2300383
4.9 (10)
58 Longs Lane Chatham Cape Cod - Sea Glass
Up to 7 guests
Vrbo$465
Booking.com$906
Average Nightly Rate
United States Massachusetts Chatham vacation rental compare prices direct by owner 2473798
4.9 (7)
Walk to Beach, Heated pool, AC, WiFi, modern coastal decor, dog friendly
Up to 10 guests
Vrbo$2,227
Booking.com
Average Nightly Rate
United States Massachusetts Dennis Port vacation rental compare prices direct by owner 2815458
4.9 (12)
Movie Room, Pool Table, Outdoor Tiki Bar, Walk to Beach, Central AC, Free Wifi
Up to 13 guests
Vrbo$1,021
Booking.com
Average Nightly Rate
  1. United States
  2. Massachusetts
  3. Orleans Vacation Rental Price Comparison

Compare Airbnb vs. Booking.com vs. Vrbo prices for vacation rentals in Orleans, MA, USA

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