Ossining Holiday Rentals

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Our top choices for Ossining holiday rentals

Ossining Vacation Rental Near River, Trails & Mta!

Ossining Vacation Rental Near River, Trails & Mta!
3.0 star property
Ossining
The price is HK$2,247
HK$6,744 total
includes taxes & fees
20 May - 21 May
Ossining Vacation Rental Near River, Trails & Mta!

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 HK$6,265
HK$10,624 total
includes taxes & fees
18 May - 19 May
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

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

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is HK$1,685
HK$2,147 total
includes taxes & fees
24 May - 25 May
1BR Queen near NYC | Trails, Biking & Sauna Bliss

Westchester Summer Pool Pet Friendly Events Games

Westchester Summer Pool Pet Friendly Events Games
2.0 star property
Ossining
The price is HK$6,071
HK$10,672 total
includes taxes & fees
18 May - 19 May
Westchester Summer Pool Pet Friendly Events Games

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 HK$1,969
HK$2,472 total
includes taxes & fees
26 May - 27 May
Polished 1BR w/ Accessible Room Features + Sauna

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 HK$548
HK$2,452 total
includes taxes & fees
18 May - 19 May
House on the Babbling Brook- Quiet 2BR + King Bed!

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, (34 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is HK$1,339
HK$2,527 total
includes taxes & fees
20 May - 21 May
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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, (13 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,276
HK$2,602 total
includes taxes & fees
25 May - 26 May
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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, (137 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is HK$1,551
HK$2,590 total
includes taxes & fees
18 May - 19 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$1,586
HK$3,085 total
includes taxes & fees
21 May - 22 May
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

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 HK$740
HK$1,056 total
includes taxes & fees
18 May - 19 May
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$1,011
HK$1,837 total
includes taxes & fees
2 Jun - 3 Jun
Cozy 1-bedroom retreat minutes from West Point!

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
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 HK$1,552
HK$4,099 total
includes taxes & fees
18 May - 19 May
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

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, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (18 reviews)
"Great place to stay! "
United States
Megan D.
The price is HK$971
HK$1,683 total
includes taxes & fees
1 Jun - 2 Jun
Piermont Oasis

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 HK$1,128
HK$2,432 total
includes taxes & fees
25 May - 26 May
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (31 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is HK$1,723
HK$3,260 total
includes taxes & fees
18 May - 19 May
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is HK$1,558
HK$1,867 total
includes taxes & fees
18 May - 19 May
Luxury home near West Point

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Excellent home, met all expectations, and attentive staff"
United States
Steve G.
The price is HK$3,430
HK$7,605 total
includes taxes & fees
19 May - 20 May
New Beach Home near Stamford Downtown/Shippan

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (91 reviews)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is HK$1,127
HK$2,490 total
includes taxes & fees
20 May - 21 May
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
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

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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Frequently asked questions

Can I find a holiday rental in Ossining?

Yes, there are holiday rentals in Ossining close to Labyrinth, or you can select a more secluded 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 are some of the best holiday rentals that Ossining has to offer?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This holiday home rental outside of Ossining is located next to a golf course, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as table football.

How many holiday rentals will I find in Ossining?

With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Ossining stay.

What’s there to see and do in Ossining?

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

What’s a holiday rental in Ossining like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossining. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.