Ossining Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Ossining vacation rentals

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 ￥64,347
￥138,701 total
includes taxes & fees
Apr 7 - Apr 8
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Villa | 5 bedrooms

Westchester Summer Pool Pet Friendly Events Games

Westchester Summer Pool Pet Friendly Events Games
2.0 star property
Ossining
The price is ￥79,854
￥162,694 total
includes taxes & fees
Apr 8 - Apr 9
Westchester Summer Pool Pet Friendly Events Games
Interior

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

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is ￥42,113
￥53,125 total
includes taxes & fees
May 3 - May 4
1BR Queen near NYC | Trails, Biking & Sauna Bliss
Interior

Near NYC! | Stylish Guestroom

Near NYC! | Stylish Guestroom
Ossining
The price is ￥46,304
￥57,615 total
includes taxes & fees
May 3 - May 4
Near NYC! | Stylish Guestroom
Interior

Polished 1BR w/ Accessible Room Features + Sauna

Polished 1BR w/ Accessible Room Features + Sauna
Ossining
6.0 out of 10, (1 review)
"We could not find location in dark and rain. Only given GPS info and no name of hotel or property. Once we arrived guard at guardhouse could not assist as we could not affirm name. When finally able to track down contact info for the vacation property company that listed the rental they had to share hotel front desk info and that’s when we learned name was Windrose On Hudson. Very stressful situation- enjoyed historical location. Great facility, not so great TV/streaming set-up… cable. "
United States
Nada S.
The price is ￥45,706
￥57,204 total
includes taxes & fees
May 3 - May 4
Polished 1BR w/ Accessible Room Features + Sauna
Villa, Garden View | Living area

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
The price is ￥42,313
￥72,185 total
includes taxes & fees
Apr 7 - Apr 8
Luxury NYC Home Game Room Free Parking
Luxury Apartment | Living area

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
10.0 out of 10, Exceptional, (2 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is ￥14,370
￥39,866 total
includes taxes & fees
Apr 19 - Apr 20
Luxury 1BR located in Prime Yonkers Area
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, (29 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is ￥22,849
￥46,076 total
includes taxes & fees
Apr 19 - Apr 20
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Luxury Apartment | Living area

Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
The price is ￥37,821
￥66,103 total
includes taxes & fees
Apr 8 - Apr 9
Luxury 3 BR Near NYC with Easy Parking
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
8.2 out of 10, Very Good, (18 reviews)
"Great location"
United States
Jordan S.
The price is ￥15,089
￥21,530 total
includes taxes & fees
Apr 7 - Apr 8
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
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, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥25,723
￥54,012 total
includes taxes & fees
Apr 14 - Apr 15
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (134 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is ￥30,018
￥42,951 total
includes taxes & fees
Apr 7 - Apr 8
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Offices

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is ￥22,992
￥49,274 total
includes taxes & fees
Apr 9 - Apr 10
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
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, (13 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is ￥32,333
￥62,900 total
includes taxes & fees
Apr 7 - Apr 8
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Luxury Duplex | Living area

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
8.0 out of 10, Very Good, (1 review)
"The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays."
United States
Adj Fatou
The price is ￥27,942
￥56,648 total
includes taxes & fees
Apr 8 - Apr 9
Uscale 2BR Escape in the Heart of NYC
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 ￥19,959
￥62,101 total
includes taxes & fees
Apr 7 - Apr 8
House on the Babbling Brook- Quiet 2BR + King Bed!
Private kitchen

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is ￥21,555
￥43,952 total
includes taxes & fees
Apr 7 - Apr 8
Charming 1-bedroom apartment in Carmel with WiFi, AC
Exterior detail

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is ￥29,560
￥80,836 total
includes taxes & fees
Apr 8 - Apr 9
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (32 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥35,926
￥66,658 total
includes taxes & fees
Apr 7 - Apr 8
Contemporary Cozy Cottage
Fridge, oven, stovetop, coffee/tea maker

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (18 reviews)
"Great Unit."
United States
Rudy R.
The price is ￥18,362
￥48,455 total
includes taxes & fees
Apr 7 - Apr 8
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
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

Royal Regency Hotel

Royal Regency Hotel

10/10 Excellent
"Was perfect for me "
Mamadou 1-night trip
Posted 2 hours ago
Royal Regency Hotel

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:

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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 in Ossining close to Labyrinth, or you can select a more remote option if you'd like a relaxing place to 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?

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!: This highly rated vacation home rental in Ossining is located near skiing and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Ossining?

With 8 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.