A wooden boardwalk winding through a forest with autumn foliage.

Ossining Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Ossining vacation rentals

Interior

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

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is ￥34,438
￥43,756 total
includes taxes & fees
Jul 28 - Jul 29
1BR Queen near NYC | Trails, Biking & Sauna Bliss
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 ￥110,466
￥194,159 total
includes taxes & fees
Jul 15 - Jul 16
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 ￥162,224
￥259,056 total
includes taxes & fees
Jul 15 - Jul 16
Summer Pool Oasis Custom Bar Arcade Pool Table
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 ￥37,025
￥46,637 total
includes taxes & fees
Jul 19 - Jul 20
Polished 1BR w/ Accessible Room Features + Sauna
Internet, bed sheets

Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
The price is ￥16,168
￥29,788 total
includes taxes & fees
Jul 15 - Jul 16
Welcome to Sweet Abby Rose!
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, (140 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥32,013
￥53,476 total
includes taxes & fees
Jul 28 - Jul 29
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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, (10 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥20,210
￥62,882 total
includes taxes & fees
Jul 21 - Jul 22
House on the Babbling Brook- Quiet 2BR + King Bed!
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 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 ￥24,616
￥42,516 total
includes taxes & fees
Jul 29 - Jul 30
Cozy 1-bedroom retreat minutes from West Point!
Exterior detail

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.
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
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
9.6 out of 10, Exceptional, (23 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is ￥22,474
￥53,295 total
includes taxes & fees
Aug 7 - Aug 8
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
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, (41 reviews)
"Room was great for the price and the host was a pleasure to deal with. "
United States
steven l.
The price is ￥30,558
￥55,998 total
includes taxes & fees
Jul 16 - Jul 17
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Property grounds

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (18 reviews)
"Great place to stay! "
United States
Megan D.
The price is ￥24,043
￥39,986 total
includes taxes & fees
Jul 21 - Jul 22
Piermont Oasis
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, (17 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥36,378
￥68,161 total
includes taxes & fees
Jul 15 - Jul 16
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
1 bedroom, iron/ironing board, free WiFi, bed sheets

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 ￥15,279
￥21,801 total
includes taxes & fees
Jul 22 - Jul 23
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
House (5 Bedrooms) | Interior

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
The price is ￥34,276
￥115,276 total
includes taxes & fees
Jul 22 - Jul 23
3 Mi to Downtown: Spacious White Plains Home
Smart TV

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
Stamford Hideaway w/ Fire Pit
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)
"loved walking the city. pizza was good."
United States
michelle b.
The price is ￥23,282
￥50,865 total
includes taxes & fees
Jul 18 - Jul 19
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is ￥43,086
￥72,384 total
includes taxes & fees
Jul 15 - Jul 16
Fabulous 3bdrm Home w/parking!
Interior

Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is ￥36,540
￥42,123 total
includes taxes & fees
Jul 22 - Jul 23
Harriman Outdoor Center - Mountain Laurel Cabin
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 ￥42,926
￥90,337 total
includes taxes & fees
Jul 15 - Jul 16
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
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

Windrose On Hudson

Windrose On Hudson

10/10 Excellent
"Nice hotel to stay st"
Igal 4-night trip
Posted 2 hours ago
Windrose On Hudson

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 Kitchawan Preserve are a couple of picturesque spots to enjoy the outdoors. Sing Sing Correctional Facility and Hudson Hills Golf Course 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.