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Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Ossining vacation homes

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

Vacation Home in Ossining

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
$806 nightly
The price is $898
Jan 5 - Jan 6, 2026
Total with taxes and fees
Foliage at Westchester Manor - Near Sleepy Hollow
Terrace/patio
House on the Babbling Brook- Quiet 2BR + King Bed!

Vacation Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (5)
"A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!"
United States
Maria L.
$333 nightly
The price is $350
Dec 22 - Dec 23
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Vacation Home in Greenwich

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
9.6 out of 10, Exceptional, (23)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
$217 nightly
The price is $245
Jan 12 - Jan 13, 2026
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
3 bedrooms, desk, iron/ironing board, free WiFi
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Vacation Home in Highland Falls

Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
$423 nightly
The price is $429
Jan 13 - Jan 14, 2026
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Property grounds
3BR West Point Retreat-3min to Back Gate+ King Bed

Vacation Home in Highland Falls

3BR West Point Retreat-3min to Back Gate+ King Bed
7.6 out of 10, Good, (5)
"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "
United States
Waylon J.
$377 nightly
The price is $427
Dec 22 - Dec 23
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
Terrace/patio
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Vacation Home in Southeast Yonkers

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
8.2 out of 10, Very Good, (18)
"Great place great location"
United States
Daquan H.
$125 nightly
The price is $147
Jan 8 - Jan 9, 2026
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Vacation Home in Carmel Hamlet

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
Dec 22 - Dec 23
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Exterior detail
Fabulous 3bdrm Home w/parking!

Vacation Home in Highland Falls

Fabulous 3bdrm Home w/parking!
9.0 out of 10, Wonderful, (4)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
$305 nightly
The price is $336
Jan 5 - Jan 6, 2026
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
Property grounds
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Vacation Home in Waterside

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
9.8 out of 10, Exceptional, (9)
"Lovely little home in Stamford."
United States
Pat A.
$313 nightly
The price is $354
Jan 8 - Jan 9, 2026
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Interior
Lovely 3BR Home with parking-Walk to WP Gate!

Vacation Home in Highland Falls

Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
$333 nightly
The price is $378
Jan 5 - Jan 6, 2026
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
Outdoor dining
45 Minutes from NYC, Entire House near Stamford Downtown,

Vacation Home in Downtown Stamford

45 Minutes from NYC, Entire House near Stamford Downtown,
10.0 out of 10, Exceptional, (21)
"Our hosts were very attentive and responsive with communications. The house is lovely, clean, well stocked and in a great location. We thoroughly enjoyed our stay!"
United States
Megan P.
$371 nightly
The price is $420
Jan 5 - Jan 6, 2026
Total with taxes and fees
45 Minutes from NYC, Entire House near Stamford Downtown,
Internet, bed sheets
Fantastic bedroom with AC & fireplace in home in charming Mount Vernon

Vacation Home in South Side

Fantastic bedroom with AC & fireplace in home in charming Mount Vernon
$119 nightly
The price is $133
Dec 28 - Dec 29
Total with taxes and fees
Fantastic bedroom with AC & fireplace in home in charming Mount Vernon
Smart TV
Peaceful Palette: 35 mins to NYC

Vacation Home in Hartsdale

Peaceful Palette: 35 mins to NYC
10.0 out of 10, Exceptional, (1)
"The house is clean, organized and well stocked for our family’s week-long stay."
United States
Wei D.
$460 nightly
The price is $526
Jan 14 - Jan 15, 2026
Total with taxes and fees
Peaceful Palette: 35 mins to NYC
Private kitchen
3BR Prime Luxury near NYC w Arcade Room

Vacation Home in Southeast Yonkers

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
$337 nightly
The price is $378
Jan 12 - Jan 13, 2026
Total with taxes and fees
3BR Prime Luxury near NYC w Arcade Room
Fridge, microwave, oven, stovetop
Contemporary Cozy Cottage

Vacation Home in Lake Peekskill

Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
$362 nightly
The price is $414
Dec 29 - Dec 30
Total with taxes and fees
Contemporary Cozy Cottage
TV, fireplace, books, offices
New Beach Home near Stamford Downtown/Shippan

Vacation Home in Cove - East Side - Shippan

New Beach Home near Stamford Downtown/Shippan
10.0 out of 10, Exceptional, (22)
"Great stay!"
United States
Kyra S.
$1,292 nightly
The price is $1,371
Jan 1 - Jan 2, 2026
Total with taxes and fees
New Beach Home near Stamford Downtown/Shippan
Fridge, microwave, oven, stovetop
Norwalk/Darien Border, 60 Min to NYC, Fire pit

Vacation Home in West Norwalk

Norwalk/Darien Border, 60 Min to NYC, Fire pit
$485 nightly
The price is $485
Jan 15 - Jan 16, 2026
Total with taxes and fees
Norwalk/Darien Border, 60 Min to NYC, Fire pit
Fridge, microwave, oven, stovetop
Stylish Beach Home near Stamford Downtown/Beach

Vacation Home in Cove - East Side - Shippan

Stylish Beach Home near Stamford Downtown/Beach
10.0 out of 10, Exceptional, (23)
"A very nice house, with excellent service and an unbeatable location. We had a great time."
Mexico
Armando V.
$1,214 nightly
The price is $1,289
Jan 1 - Jan 2, 2026
Total with taxes and fees
Stylish Beach Home near Stamford Downtown/Beach
Beach nearby, sun loungers, beach towels
Fun, Friends, and Family Lakefront Home w/Dock and Beach

Vacation Home in Mahopac

Fun, Friends, and Family Lakefront Home w/Dock and Beach
10.0 out of 10, Exceptional, (12)
"Super convenient location :)"
United States
Sean M.
$714 nightly
The price is $774
Jan 12 - Jan 13, 2026
Total with taxes and fees
Fun, Friends, and Family Lakefront Home w/Dock and Beach
TV
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Vacation Home in Cove - East Side - Shippan

Spacious 3 Bd Home Pet Friendly, Parking and Laundry
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.
$508 nightly
The price is $548
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spacious 3 Bd Home Pet Friendly, Parking and Laundry
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
"Things were in good shape and working correctly "
Troy 5-night trip
Posted 17 hours ago
Sonesta Simply Suites Nanuet

Find out more about Ossining

Ossining Vacation Homes information

Number of reviews
191
Accommodation
325 Vacation Homes
Lowest Price
$133
Highest Price
$1,371

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