Vacation rentals in Orleans
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Top-rated vacation rentals in Orleans
Guests agree: these stays are highly rated for location, cleanliness, and more.
Guest suite in Chatham
4.94 out of 5 average rating, 140 reviewsThe Captain Kimball House of Christmas Joy
Experience Cape Cod while staying in this historic 1735 Salt Box built by Captain Kimball Eldredge. You will have a private entrance and the entire second floor dwelling to yourself. Conveniently located on 28 with just a short walk to the beach, this recently renovated home showcases colonial craftsmanship with the original wood floors and fireplaces. Two restaurants a stones throw away, the Cape Cod Rail Trail down the street and only a five minute drive to downtown Chatham or Harwich Port.
May 3 – 10
Condo in Chatham
4.96 out of 5 average rating, 277 reviewsIn-town, Pied-a-Terre. Private, Sunny condo.
Bright, Sunny, fabulous in-town location. CLEAN, SAFE & PRIVATE hidden ABOVE shops, behind the Main Post Office. Great for Romantic Getaway, business trips, overflow guests. Comfortably furnished, thoughtfully outfitted. Quality linens, duvet etc. Walk to restaurants, cafe/bakery, groceries, shops, ballpark, Oyster Pond Beach, CBI, tennis courts, bike path, bike rental, etc etc. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**
Dec. 14 – 21
Cottage in Orleans
4.93 out of 5 average rating, 128 reviewsCape Cod Cottage with view of Orleans Town Cove
The cottage is very clean, cute and comfortable and has every thing you might need. Situated in a quiet, friendly little neighborhood, right next to the famous Cottage Street Bakery, yet you would never know you are so close to town! It is centrally located within walking distance to restaurants, shops and bike path, with the Ice Cream Cafe right down the street on the corner. 3 miles to all beaches. Access to the Cove including kayak rental is just down the street. Perfect location!
Apr. 12 – 19
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Popular amenities for Orleans vacation rentals
Other great vacation rentals in Orleans
Condo in Dennis
4.96 out of 5 average rating, 144 reviewsStudio, 300 yards to Glendon, Mermaid Haven #1
Oct. 14 – 21
Home in Chatham
4.96 out of 5 average rating, 189 reviewsStudio cottage in Chatham Ma.
Nov. 23 – 30
Cottage in Eastham
4.95 out of 5 average rating, 204 reviewsThe Breeze Overlooking Minister's Pond
Apr. 18 – 25
Cottage in East Orleans
4.95 out of 5 average rating, 107 reviewsDistiller’s Cottage Nauset Beach East Orleans, MA
Sep. 8 – 15
Tiny homes in Wellfleet
4.98 out of 5 average rating, 226 reviewsWriter's Cabin in Woods near Wellfleet Bay
Jun. 8 – 15
Home in Brewster
4.95 out of 5 average rating, 137 reviewsBrewster Home on Lower Mill Pond
Feb. 25 – Mar. 4
Apartment in Eastham
4.88 out of 5 average rating, 244 reviewsCape Cod Suite Near Private Beach
Nov. 13 – 20
Cottage in Orleans
4.98 out of 5 average rating, 59 reviewsHobbit Cottage with Marsh View
Nov. 12 – 19
Guest suite in Orleans
4.95 out of 5 average rating, 79 reviewsSpacious Guest Suite Close to Town
Apr. 11 – 18
Cabin in Brewster
4.98 out of 5 average rating, 58 reviewsCozy Cape Cabin
May 8 – 15
Guest suite in Eastham
4.99 out of 5 average rating, 97 reviewsBeautiful Cape Cod location - Bay, Ocean, and Pond
May 12 – 19
Home in Orleans
4.96 out of 5 average rating, 25 reviewsGorgeous Renovation Walk to Water!
Oct. 21 – 28
Quick stats about vacation rentals in Orleans
Total rentals | 410 properties |
---|---|
Rentals with dedicated workspaces | 130 properties have a dedicated workspace |
Rentals with a pool | 30 properties have a pool |
Pet-friendly rentals | 130 properties allow pets |
Family-friendly rentals | 340 properties are a good fit for families |
Total number of reviews | 9.8K reviews |
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