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Search Vacation Homes in Ossining

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Vacation Homes in Ossining

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
$926 nightly
The price is $1,031
Nov 12 - Nov 13
Total with taxes and fees
Foliage at Westchester Manor - Near Sleepy Hollow
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
9.0 out of 10, Wonderful, (6)
"This is an incredibly unique property with some upsides. It is a cool old (1920's) Tudor style house that is well-suited for large groups. While it was fine for a couple of nights, any longer would have made the downsides (deferred maintenance, insufficient silverware, stained carpeting) less tolerable. There were also some communication issues with the property management company and the host during the stay. Specifically, we counted on there being a crib available, as it was specified in the...
United States
Marnie O.
$1,346 nightly
The price is $1,390
Dec 2 - Dec 3
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
9.6 out of 10, Exceptional, (20)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
$181 nightly
The price is $205
Nov 9 - Nov 10
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
10.0 out of 10, Exceptional, (6)
"Exceptional space for our needs. We’d absolutely book again if the opportunity arises. Maritza was communicative and everything was easily accessible"
United States
Joanne
$291 nightly
The price is $329
Nov 7 - Nov 8
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
3BR West Point Retreat-3min to Back Gate+ King Bed
9.4 out of 10, Exceptional, (3)
"Home was very peaceful and serene, My Boys really enjoyed the relaxing and laid back vibe this stay had to offer. My kids did mention it would be a summer vacation stay, because of the creek in the back. Overall is was clean and accommodating. Host did their best for all my accommodation. I would give them a 5- Star White Glove on this. Thanks, Hope to revisit! "
United States
Akail S.
$397 nightly
The price is $449
Nov 11 - Nov 12
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
Private room, 5 min walk to restaurant, 40 min to NYC. 5 min drive to MetroNorth
2.0 star property
$120 nightly
The price is $137
Nov 7 - Nov 8
Total with taxes and fees
Private room, 5 min walk to restaurant, 40 min to NYC. 5 min drive to MetroNorth
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
$328 nightly
The price is $355
Nov 13 - Nov 14
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7)
"Celebrated my son’s HS graduation with my father-in-law along for the adventure, Joe’s townhouse is super convenient to Thayer Gate and eating establishments along Main St. Grill worked well and the beds made for sound slumber. For mixed company an extra half bath might be desired, but 3 guys who know each other well managed just fine. The basement washer & dryer are top of line."
United States
James W.
$311 nightly
The price is $352
Nov 17 - Nov 18
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
$367 nightly
The price is $420
Nov 10 - Nov 11
Total with taxes and fees
Contemporary Cozy Cottage
Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
$470 nightly
The price is $477
Nov 17 - Nov 18
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Fabulous 3bdrm Home w/parking!
8.0 out of 10, Very Good, (2)
"Great place. Close to West Point activity. Clean and new."
United States
Joanne V.
$297 nightly
The price is $327
Nov 17 - Nov 18
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
NJ New Construction Luxury Home - Minutes to NYC - Vacation or Staycation
2.0 star property
7.6 out of 10, Good, (5)
"Clean, spacious 5 bedroom home. The home had plenty of room, numerous TVs, and a great location to Metlife Stadium. My family really enjoyed our stay."
United States
Larry M.
$1,747 nightly
The price is $1,927
Nov 9 - Nov 10
Total with taxes and fees
NJ New Construction Luxury Home - Minutes to NYC - Vacation or Staycation
45 Minutes from NYC, Entire House near Stamford Downtown,
10.0 out of 10, Exceptional, (19)
"Very nice property. Owner was very nice and quickly answered any questions we had. Well stocked pantry and fridge!! We enjoyed our stay and property was very convenient and comfortable. "
United States
Lisa B.
$401 nightly
The price is $454
Nov 10 - Nov 11
Total with taxes and fees
45 Minutes from NYC, Entire House near Stamford Downtown,
Fun, Friends, and Family Lakefront Home w/Dock and Beach
10.0 out of 10, Exceptional, (12)
"Super convenient location :)"
United States
Sean M.
$672 nightly
The price is $728
Nov 9 - Nov 10
Total with taxes and fees
Fun, Friends, and Family Lakefront Home w/Dock and Beach
3BR Prime Luxury near NYC w Arcade Room
2.0 star property
8.0 out of 10, Very Good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveler
$687 nightly
The price is $769
Nov 7 - Nov 8
Total with taxes and fees
3BR Prime Luxury near NYC w Arcade Room
Stylish Beach Home near Stamford Downtown/Beach
10.0 out of 10, Exceptional, (23)
"We had an absolutely amazing time during our stay. The house was beautiful, and Elena was super quick & helpful with answering any questions we had. Both the check in and check out processes were easy and smooth. We had a great time and would highly recommend staying here!"
United States
Matthew O.
$805 nightly
The price is $856
Nov 9 - Nov 10
Total with taxes and fees
Stylish Beach Home near Stamford Downtown/Beach
Luxury NY Home with Free Parking
4.0 star property
$558 nightly
The price is $638
Nov 7 - Nov 8
Total with taxes and fees
Luxury NY Home with Free Parking
West Point Villa - Jacuzzi Pool BBQ Games Pets
2.0 star property
$603 nightly
The price is $713
Nov 11 - Nov 12
Total with taxes and fees
West Point Villa - Jacuzzi Pool BBQ Games Pets
6 BR, 4 BA Mansion Close to the City
10.0 out of 10, Exceptional, (1)
"Awesome space, perfect for our fall getaway, close to NYC or small town shopping"
United States
Jennifer L.
$680 nightly
The price is $801
Nov 10 - Nov 11
Total with taxes and fees
6 BR, 4 BA Mansion Close to the City
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ossining Hotel Reviews

Find out more about Ossining

Ossining Vacation Homes information

Number of reviews
141
Accommodation
327 Vacation Homes
Lowest Price
$205
Highest Price
$1,927

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