Vacation rentals in Ossining

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Top-rated vacation rentals in Ossining

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Apartment in Mount Kisco
Cozy 1 Bdrm Apt; Privt Entry; 5 min walk to train
This cozy apartment is on the lower level of a house, just a 5 minute walk to town and the Harlem Line, Metro North Train stop. A separate entrance to the apt offers complete privacy. This gorgeous space has a fully equipped kitchen, bathroom, comfy twin beds . Located in the adorable town of Mount Kisco, allowing you to take strolls to access restaurants, boutique shops, library, park and bars. It has the feel of a country retreat, a quaint town, and it's an easy commute to White Plains or NYC.
Aug. 19 – 26
$192 CAD per night
4.93 out of 5 average rating, 146 reviews
Guest favourite
Cottage in Cortlandt
Cottage at Peekskill Hollow
Romantic Hudson Valley cottage just 1 hour outside NYC in northern Westchester! Beautiful, wooded location along the Peekskill Hollow Creek - just off the beaten path. You’ll be surrounded by nature and still be a hop, skip and jump away from restaurants, shopping, hiking/bike trails, West Point, the Hollow Brook Golf Club and historic sites (Revolutionary War, Rockefeller, Roosevelt, Underground Railroad). Quick access (by car or train) to/from NYC and greater Hudson Valley. High speed WiFi.
May 6 – 13
$370 CAD per night
5.0 out of 5 average rating, 102 reviews
Superhost
Home in Ossining
Lower Hudson Valley Idyllic Retreat
Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.
Aug. 22 – 29
$598 CAD per night
4.84 out of 5 average rating, 123 reviews

Popular amenities for Ossining vacation rentals

Stay near Ossining's top sights

3 Westerly Bar and Grill15 locals recommend
DD's Diner8 locals recommend
Stop & Shop7 locals recommend
The Boathouse23 locals recommend
Los Abuelos Restaurant5 locals recommend
Landmark Diner3 locals recommend

Other great vacation rentals in Ossining

Guest favourite
Guest suite in Stamford
Tranquil Retreat in North Stamford
Nov. 4 – 11
$147 CAD per night
4.93 out of 5 average rating, 110 reviews
Guest favourite
Cottage in Mohegan Lake
The Pearl of Westchester
May 28 – Jun. 4
$282 CAD per night
4.93 out of 5 average rating, 164 reviews
Superhost
Home in Peekskill
The Peekskill RiverView House
Jul. 24 – 31
$588 CAD per night
4.89 out of 5 average rating, 149 reviews
Guest favourite
Cottage in Greenwood Lake
Luxury Cottage with Spectacular Lake Views
Nov. 2 – 9
$506 CAD per night
4.97 out of 5 average rating, 268 reviews
Superhost
Apartment in Peekskill
Little haven by the woods
Oct. 17 – 24
$212 CAD per night
4.84 out of 5 average rating, 113 reviews
Guest favourite
Home in Dobbs Ferry
Small cozy room in historic 1828 Dobbs Ferry home.
Nov. 4 – 11
$84 CAD per night
4.93 out of 5 average rating, 298 reviews
Guest favourite
Barn in Mount Kisco
NY Rustic Cottage Getaway
May 13 – 20
$228 CAD per night
4.91 out of 5 average rating, 538 reviews
Guest favourite
Home in Nyack
Chic Vintage Cottage in Artsy Village of Nyack
Aug. 27 – Sep. 3
$397 CAD per night
4.95 out of 5 average rating, 149 reviews
Guest favourite
Cottage in Cortlandt
The Little Cottage in the Woods
Jun. 19 – 26
$207 CAD per night
4.99 out of 5 average rating, 157 reviews
Superhost
Villa in Ossining
7BR Beacon Family Retreat: Jacuzzi, BBQ, Games!
Feb. 6 – 13
$1,128 CAD per night
4.96 out of 5 average rating, 67 reviews
Guest favourite
Guest suite in Haverstraw
Unique comfortable guest suite
Feb. 16 – 23
$126 CAD per night
5.0 out of 5 average rating, 21 reviews
Guest favourite
Guest suite in Croton-on-Hudson
Enchanting Farmhouse Suite w/ pool and sauna
Jun. 20 – 27
$295 CAD per night
4.99 out of 5 average rating, 89 reviews

Quick stats about vacation rentals in Ossining

Total rentals

30 properties

Wifi availability

30 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

1.5K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Westchester County
  5. Ossining