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Vacation Homes in Ossining

House | 5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow

2.0 star property
Ossining
$926 nightly
The price is $1,031
Nov 12 - Nov 13
Total with taxes and fees
Foliage at Westchester Manor - Near Sleepy Hollow
Outdoor banquet area
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Ossining
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!
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Greenwich
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.
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls
10.0 out of 10, Exceptional, (2)
"Good stay, awesome place"
United States
Scott G.
$350 nightly
The price is $370
Nov 12 - Nov 13
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
Property grounds
3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed

Highland Falls
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.
$390 nightly
The price is $441
Nov 11 - Nov 12
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Carmel Hamlet
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.
Interior
Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!

Highland Falls
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!
Property grounds
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterside
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
$294 nightly
The price is $332
Nov 17 - Nov 18
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Highland Falls
10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
$464 nightly
The price is $471
Nov 17 - Nov 18
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!

Highland Falls
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!
Exterior
NJ New Construction Luxury Home - Minutes to NYC - Vacation or Staycation

NJ New Construction Luxury Home - Minutes to NYC - Vacation or Staycation

2.0 star property
River Edge
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
Outdoor dining
45 Minutes from NYC, Entire House near Stamford Downtown,

45 Minutes from NYC, Entire House near Stamford Downtown,

Downtown Stamford
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.
$376 nightly
The price is $425
Nov 10 - Nov 11
Total with taxes and fees
45 Minutes from NYC, Entire House near Stamford Downtown,
Interior
Contemporary Cozy Cottage

Contemporary Cozy Cottage

Lake Peekskill
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
Property grounds
Fun, Friends, and Family Lakefront Home w/Dock and Beach

Fun, Friends, and Family Lakefront Home w/Dock and Beach

Mahopac
10.0 out of 10, Exceptional, (12)
"Super convenient location :)"
United States
Sean M.
$672 nightly
The price is $728
Nov 10 - Nov 11
Total with taxes and fees
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Private kitchen
6 BR, 4 BA Mansion Close to the City

6 BR, 4 BA Mansion Close to the City

Getty Square
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
Property grounds
Waterfront Retreat Center for Health & Wellness

Waterfront Retreat Center for Health & Wellness

New Rochelle
9.6 out of 10, Exceptional, (64)
"This historic home was better than I could have hoped for. My extended family thoroughly enjoyed this beautiful home. Every room was a joy to be in. We would go back in a heart beat."
United States
Kathy L.
$2,048 nightly
The price is $2,342
Nov 12 - Nov 13
Total with taxes and fees
Waterfront Retreat Center for Health & Wellness
TV
Ideal Work/Family Stay Ample Parking & + Near I95

Ideal Work/Family Stay Ample Parking & + Near I95

Cove - East Side - Shippan
9.4 out of 10, Exceptional, (3)
"the home was nice clean if in the area I would stay here again"
United States
james w.
$481 nightly
The price is $518
Nov 11 - Nov 12
Total with taxes and fees
Ideal Work/Family Stay Ample Parking & + Near I95
House | 7 bedrooms
West Point Villa - Jacuzzi Pool BBQ Games Pets

West Point Villa - Jacuzzi Pool BBQ Games Pets

2.0 star property
Cornwall
$603 nightly
The price is $713
Nov 11 - Nov 12
Total with taxes and fees
West Point Villa - Jacuzzi Pool BBQ Games Pets
Terrace/patio
New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan

Cove - East Side - Shippan
10.0 out of 10, Exceptional, (21)
"We had about 14 guests sleep comfortably here and all enjoyed our time and the amenities immensely."
United States
Matthew L.
$799 nightly
The price is $849
Nov 11 - Nov 12
Total with taxes and fees
New Beach Home near Stamford Downtown/Shippan
TV
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

West Side
9.2 out of 10, Wonderful, (5)
"It’s nice to have a place for our family of 5 that actually fits us all. Plenty of space and very clean. Thanks "
United States
Katy G.
$468 nightly
The price is $503
Nov 9 - Nov 10
Total with taxes and fees
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
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

Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

10/10 Excellent
"My room and bathroom were spotless! We enjoyed many relaxing bubble baths. Excellent water pressure too. As a spine patient, I was concerned about the mattress. However, the bed was excellent and I slept great without additional morning pain. The staff is very nice and accommodating. The gym and laundry rooms were always clean and they have plenty of machines. The location is perfect. Costco is in walking distance next door. If you don’t feel like cooking, there are many restaurants in the area to choose from. We enjoyed our stay and look forward to our next accommodations."
Jennifer 1-night trip
Posted 3 days ago
Sonesta Simply Suites Nanuet

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