Boardwalk over marshland on the trail at Teatown Lake Reservation in Ossining, New York.

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Ossining vacation homes

Outdoor banquet area

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
9.2 out of 10, Wonderful, (7 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is AED 3,030
AED 5,090 total
includes taxes & fees
23 Jun - 24 Jun
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
House | 5 bedrooms

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is AED 3,816
AED 6,038 total
includes taxes & fees
23 Jun - 24 Jun
Summer Pool Oasis Custom Bar Arcade Pool Table
Property grounds

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (40 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AED 575
AED 1,113 total
includes taxes & fees
24 Jun - 25 Jun
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Terrace/patio

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, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AED 459
AED 1,429 total
includes taxes & fees
21 Jun - 22 Jun
House on the Babbling Brook- Quiet 2BR + King Bed!
Living area

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is AED 536
AED 1,318 total
includes taxes & fees
8 Jul - 9 Jul
Stamford Hideaway w/ Fire Pit
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
9.8 out of 10, Exceptional, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is AED 823
AED 1,531 total
includes taxes & fees
25 Jun - 26 Jun
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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, (14 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is AED 826
AED 1,549 total
includes taxes & fees
21 Jun - 22 Jun
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Terrace/patio

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is AED 347
AED 495 total
includes taxes & fees
21 Jun - 22 Jun
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Terrace/patio

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
9.8 out of 10, Exceptional, (7 reviews)
"We had such a nice and peaceful stay! Shelton’s place was super clean, quiet, comfortable, and had everything we needed. Would definitely stay here again! "
United States
Katie M.
The price is AED 558
AED 1,315 total
includes taxes & fees
14 Jul - 15 Jul
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is AED 826
AED 1,542 total
includes taxes & fees
30 Jun - 1 Jul
Contemporary Cozy Cottage
In-room safe, iron/ironing board, travel crib, free WiFi

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
Bryn Mawr
The price is AED 1,488
AED 2,708 total
includes taxes & fees
21 Jun - 22 Jun
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
Terrace/patio

Spacious 3BR Home • Free Parking • Convenient NYC Access • Perfect for Families

Spacious 3BR Home • Free Parking • Convenient NYC Access • Perfect for Families
Southeast Yonkers
The price is AED 1,157
AED 2,292 total
includes taxes & fees
21 Jun - 22 Jun
Spacious 3BR Home • Free Parking • Convenient NYC Access • Perfect for Families
Smart TV

Cozy 4BR Home • Free Street Parking • Quick NYC Access • Perfect for Families

Cozy 4BR Home • Free Street Parking • Quick NYC Access • Perfect for Families
Southeast Yonkers
The price is AED 1,157
AED 2,292 total
includes taxes & fees
21 Jun - 22 Jun
Cozy 4BR Home • Free Street Parking • Quick NYC Access • Perfect for Families
Interior

Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
The price is AED 981
AED 1,124 total
includes taxes & fees
24 Jun - 25 Jun
Harriman Outdoor Center - Cranberry Cabin
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 reviews)
"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.
The price is AED 1,017
AED 1,743 total
includes taxes & fees
22 Jun - 23 Jun
Lovely 3BR Home with parking-Walk to WP Gate!
Interior

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.2 out of 10, Wonderful, (25 reviews)
"House was amazing, with a wonderful view. Hosts were responsive and helpful. Will need to come back in summer!"
United States
Scott H.
The price is AED 1,756
AED 3,507 total
includes taxes & fees
24 Jun - 25 Jun
Waterview House Walking Distance from Cove Beach
Property grounds

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

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very Good, (6 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is AED 786
AED 2,015 total
includes taxes & fees
23 Jun - 24 Jun
3BR West Point Retreat-3min to Back Gate+ King Bed
Beach nearby, sun loungers, beach towels

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, (16 reviews)
"Very clean and cozy home "
United States
Brian D.
The price is AED 1,306
AED 2,753 total
includes taxes & fees
22 Jun - 23 Jun
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.6 out of 10, Exceptional, (7 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is AED 1,088
AED 1,782 total
includes taxes & fees
14 Jul - 15 Jul
Fabulous 3bdrm Home w/parking!
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

La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

10/10 Excellent
"Inexpensive clean, not the most glamorous place, but for the price it was appropriate. I would go back again and I would recommend for someone who is looking for something within their budget. Staff was friendly as well thank you."
Kingsley 1-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Stamford / New York City