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Ossining Vacation Rentals

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Check prices for these dates

Tonight
Jan 7 - Jan 8
Tomorrow
Jan 8 - Jan 9
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Ossining vacation rentals

Interior
1BR Queen near NYC | Trails, Biking & Sauna Bliss

Aparthotel in Ossining

1BR Queen near NYC | Trails, Biking & Sauna Bliss
2.0 star property
The price is ￥44,827
￥57,676 total
includes taxes & fees
Jan 8 - Jan 9
1BR Queen near NYC | Trails, Biking & Sauna Bliss
House | 5 bedrooms
NEW 45 Wolden Rd Ossining NY 10562

Vacation Home in Ossining

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
The price is ￥47,223
￥125,879 total
includes taxes & fees
Jan 12 - Jan 13
NEW 45 Wolden Rd Ossining NY 10562
Outdoor banquet area
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Vacation Home in Ossining

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
9.2 out of 10, Wonderful, (7)
"Communication was excellent. The house itself is older and fine for its age, but "
United States
Jonathan O.
The price is ￥68,125
￥141,901 total
includes taxes & fees
Jan 28 - Jan 29
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Interior
Polished 1BR w/ Accessible Room Features + Sauna

Aparthotel in Ossining

Polished 1BR w/ Accessible Room Features + Sauna
2.0 star property
The price is ￥44,827
￥58,049 total
includes taxes & fees
Jan 9 - Jan 10
Polished 1BR w/ Accessible Room Features + Sauna
Interior
Near NYC! | Stylish Guestroom

Aparthotel in Ossining

Near NYC! | Stylish Guestroom
2.0 star property
The price is ￥48,742
￥61,914 total
includes taxes & fees
Jan 9 - Jan 10
Near NYC! | Stylish Guestroom
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.
The price is ￥15,660
￥64,273 total
includes taxes & fees
Jan 8 - Jan 9
Sleek Escape: Modern 3 BR- 4 Min from West Point !
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)
"Good stay, awesome place"
United States
Scott G.
The price is ￥13,155
￥50,456 total
includes taxes & fees
Jan 12 - Jan 13
House on the Babbling Brook- Quiet 2BR + King Bed!
Fridge, oven, stovetop, coffee/tea maker
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Apartment in Highland Falls

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.8 out of 10, Exceptional, (15)
"Great Unit."
United States
Rudy R.
The price is ￥12,371
￥41,176 total
includes taxes & fees
Jan 12 - Jan 13
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
3 bedrooms, desk, iron/ironing board, travel crib
Local Artist Inspired | Walk to WestPoint + King Bed

Apartment in Highland Falls

Local Artist Inspired | Walk to WestPoint + King Bed
9.2 out of 10, Wonderful, (10)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is ￥13,311
￥60,078 total
includes taxes & fees
Jan 12 - Jan 13
Local Artist Inspired | Walk to WestPoint + King Bed
Living area
Luxe 1BR Oasis - Prime NY Stay

Apartment in Bryn Mawr

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
The price is ￥17,226
￥42,606 total
includes taxes & fees
Jan 22 - Jan 23
Luxe 1BR Oasis - Prime NY Stay
Living area
Single Family 3BR Home Game Room Parking

Villa in Bryn Mawr

Single Family 3BR Home Game Room Parking
4.0 star property
Single Family 3BR Home Game Room Parking
TV
Cozy 1-bedroom retreat minutes from West Point!

Apartment in Highland Falls

Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ￥14,635
￥29,691 total
includes taxes & fees
Feb 2 - Feb 3
Cozy 1-bedroom retreat minutes from West Point!
Desk, free WiFi, bed sheets
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Apartment in Croton-on-Hudson

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
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, (24)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
The price is ￥20,085
￥41,422 total
includes taxes & fees
Jan 12 - Jan 13
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Smart TV, video games, DVD player, books
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Apartment in Croton-on-Hudson

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
10.0 out of 10, Exceptional, (6)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Smart TV
Modern Luxe 1BR Apt in Downtown Stamford

Apartment in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
9.6 out of 10, Exceptional, (5)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is ￥21,141
￥57,120 total
includes taxes & fees
Jan 11 - Jan 12
Modern Luxe 1BR Apt in Downtown Stamford
Private kitchen
Luxury 1BR located in Prime Yonkers Area

Apartment in Bryn Mawr

Luxury 1BR located in Prime Yonkers Area
2.0 star property
The price is ￥15,503
￥40,678 total
includes taxes & fees
Jan 22 - Jan 23
Luxury 1BR located in Prime Yonkers Area
Private kitchen
Modern Luxury 1BR Stamford Getaway

Apartment in Downtown Stamford

Modern Luxury 1BR Stamford Getaway
10.0 out of 10, Exceptional, (1)
"The apartment is located in the hub bub of Stamford, a nice area very populated even in the evening where it feels safe. Apartment had all amenities that I needed. The host provided extra touches like a Keurig coffee pot stocked with Keurig cups and sugar. A washing machine and dryer were a plus as I like to pack only clean clothes. Bed was super comfortable. Modern design has a Zen vibe, great to decompress after travel. TV offered free movies that didn’t require my own subscription which...
United States
Debbie N.
The price is ￥25,839
￥49,133 total
includes taxes & fees
Jan 15 - Jan 16
Modern Luxury 1BR Stamford Getaway
Fridge, microwave, oven, stovetop
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Apartment in Highland Falls

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is ￥26,968
￥45,616 total
includes taxes & fees
Feb 4 - Feb 5
Beautiful First Flr, 2-Bedroom Apt w/ Free 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

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"I had an amazing experience! The room was clean, the staff were very kind and the food was great. "
Natasha 1-night trip
Posted 1 day ago
Hyatt Regency Greenwich

Find out more about Ossining

Search for holiday rentals in Ossining on Expedia! You can easily find your home rentals, villas, holiday apartments in Ossining using one of the methods below:

  • View our selection of featured holiday rentals in Ossining
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Look no further and take a look at our great range of rental properties in Ossining!

Frequently asked questions

Can I find a vacation rental in Ossining?

Yes, there are vacation rentals close to well known attractions in Ossining, or you can go with a more remote option if you're looking for a relaxing stay. Ossining is known for its restaurants and parks. Make sure you have time to check out the golf courses and university setting during your trip.

What's the top vacation rental that Ossining has to offer?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: Visitors like this Ossining vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Ossining?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Ossining stay.

What’s there to see and do in Ossining?

Cultural attractions include Sing Sing Prison Museum and Ossining Historical Society, whereas Teatown Lake Reservation and Merchants Square are a couple of picturesque spots to enjoy the outdoors. Sing Sing Correctional Facility and Thomas J. Watson Research Center are other places to visit while you're in town.

What’s a vacation rental in Ossining like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Ossining. Vacation rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for families.