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 favourite
Condo in Brewster
Shining Sea Condo
Ocean Edge condo with cathedral ceilings! Beautiful private deck located on the 5th hole of the Ocean Edge golf course! Located within the Eaton village. Two queen beds along with pullout couch allows 6 to sleep comfortably within the unit. Linens are included!! Large kitchen with washer/ dryer, AC in living room and heat throughout the unit. Wifi and two smart TVs with ROKU devices. Flexible dates allows guests to stay whatever length they would like instead of a mandatory week. Come enjoy!
Jan. 19 – 26
$166 CAD per night
4.86 out of 5 average rating, 152 reviews
Guest favourite
Cottage in Eastham
The Breeze Overlooking Minister's Pond
Welcome to an absolutely spotless, pristine, romantic cottage directly on a freshwater pond. Centrally located in beautiful Eastham, the Breeze is within walking distance to the Salt Pond Museum and Visitor Center and hiking trails. Take one of the electric bikes provided and hop on the bike path (the CCRT) which is just down the street. Kayak or canoe on the pond. Featured on WNAV "Romantic Winter Getaways". Award winning recommendations guide provided with each stay. *Sat-Sat in July & Au
Apr. 20 – 27
$329 CAD per night
4.95 out of 5 average rating, 204 reviews
Guest favourite
Cottage in Orleans
Cape 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!
Nov. 12 – 19
$480 CAD per night
4.93 out of 5 average rating, 128 reviews

Popular amenities for Orleans vacation rentals

Stay near Orleans's top sights

Wequassett Resort and Golf Club59 locals recommend
Hot Chocolate Sparrow58 locals recommend
Cape Escape Adventure Golf25 locals recommend
the knack51 locals recommend
Land Ho85 locals recommend
Hole In One Breakfast & Lunch47 locals recommend

Other great vacation rentals in Orleans

Guest favourite
Home in Orleans
Gorgeous Renovation Walk to Water!
Sep. 30 – Oct. 7
$948 CAD per night
4.96 out of 5 average rating, 25 reviews
Guest favourite
Cottage in Orleans
Hobbit Cottage with Marsh View
Nov. 13 – 20
$265 CAD per night
4.98 out of 5 average rating, 59 reviews
Guest favourite
Guest suite in Orleans
Spacious Guest Suite Close to Town
Mar. 25 – Apr. 1
$221 CAD per night
4.95 out of 5 average rating, 79 reviews
Guest favourite
Home in Orleans
4 Season Cottage, Nauset Beach, tennis court
Oct. 11 – 18
$556 CAD per night
5.0 out of 5 average rating, 59 reviews
Guest favourite
Home in Orleans
Cape Cod Charmer
Aug. 24 – 31
$846 CAD per night
5.0 out of 5 average rating, 47 reviews
Guest favourite
Cabin in Brewster
Cozy Cape Cabin
May 8 – 15
$225 CAD per night
4.98 out of 5 average rating, 58 reviews
Guest favourite
Home in Orleans
Antique Cottage with Path to Arey’s Pond
Nov. 5 – 12
$338 CAD per night
4.9 out of 5 average rating, 10 reviews
Guest favourite
Home in Orleans
Settle into an Authentic Cape Cod with Central A/C
Jan. 11 – 18
$669 CAD per night
4.99 out of 5 average rating, 74 reviews
Guest favourite
Cottage in Orleans
Escape to this Peaceful Cottage near Nauset Beach
Apr. 18 – 25
$319 CAD per night
4.89 out of 5 average rating, 46 reviews
Guest favourite
Home in Orleans
Contemporary Post & Beam "Barn"
May 16 – 23
$379 CAD per night
4.94 out of 5 average rating, 67 reviews
Superhost
Home in Orleans
East Orleans Historic Home- Unit 3
May 9 – 16
$579 CAD per night
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Orleans
E Orleans B/W 2 Ocean Beaches! Pets OK! No fees!
Oct. 30 – Nov. 6
$969 CAD per night
4.94 out of 5 average rating, 18 reviews

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

Destinations to explore