Ossining Vacation Rentals from $177: Search Short-Term Rentals

Q: 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.

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Our top choices for Ossining vacation rentals

Coffee/tea maker, fridge, microwave, stovetop

1. NYC-Area Escape Near River, Trails & MTA!

Ossining

Justeen P.

2. Nyc-area Escape Near River, Trails & Mta!

Ossining

3. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

Ossining

$283 nightly

Sep 27 - Sep 28

Total with taxes and fees

4. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

$1,107 nightly

Sep 22 - Sep 23

Total with taxes and fees

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

Ossining

natalie l.

$969 nightly

Sep 22 - Sep 23

Total with taxes and fees

6. Polished 1BR w/ Accessible Room Features + Sauna

Ossining

"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. "

Nada S.

$289 nightly

Sep 27 - Sep 28

Total with taxes and fees

7. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Croton-on-Hudson

Ann S.

$249 nightly

Sep 22 - Sep 23

Total with taxes and fees

Smart TV, video games, DVD player, books

8. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Croton-on-Hudson

Mateo A.

$359 nightly

Sep 24 - Sep 25

Total with taxes and fees

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

CROTON HDSN

Aimee S.

$328 nightly

Oct 4 - Oct 5

Total with taxes and fees

10. Piermont Oasis

Piermont

Megan D.

$179 nightly

Sep 28 - Sep 29

Total with taxes and fees

11. 1 Queen Bed | Smoking

Elmsford

$119 nightly

Sep 22 - Sep 23

Total with taxes and fees

Coffee/tea maker, fridge, oven, stovetop

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

Highland Falls

Andrew L.

$285 nightly

Sep 22 - Sep 23

Total with taxes and fees

13. House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls

Leann M.

$378 nightly

Sep 22 - Sep 23

Total with taxes and fees

14. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery

Jasmine

$280 nightly

Sep 22 - Sep 23

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

15. Contemporary Cozy Cottage

Lake Peekskill

Aj L.

$367 nightly

Sep 30 - Oct 1

Total with taxes and fees

16. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Christopher J.

$275 nightly

Oct 5 - Oct 6

Total with taxes and fees

1 bedroom, iron/ironing board, WiFi (free), bed sheets

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

Southeast Yonkers

Jordan S.

$115 nightly

Sep 23 - Sep 24

Total with taxes and fees

18. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Putnam Valley

Heather T.

$413 nightly

Sep 23 - Sep 24

Total with taxes and fees

19. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Greenwich

"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...

Kathleen W.

$199 nightly

Sep 25 - Sep 26

Total with taxes and fees

20. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterside

Leslie S.

$297 nightly

Oct 20 - Oct 21

Total with taxes and fees

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Top Ossining Hotel Reviews

LIV Hotel Bronx - Newly Built

10/10 Excellent

"This place is very cool and staff is helpful Ben is Great 🙏"

Royal Regency Hotel

8/10 Good

"Overall, everything was very good. Unfortunately, the freezer in the refrigerator didn't work properly and I had something that needed to be kept frozen and that didn't work. The lighting in the bathrooms could be improved, not good at all. Walls weren't the greatest for noise and we could hear several of our neighboring rooms, at times. Staff was very accommodating and polite and breakfast was excellent. The last thing, nothing was noted at check in about the use of your room key to get in and out of the parking lot. We figured it out, but a little heads up would have been nice. Overall, a nice stay with just a few minor issues."

Hampton Inn White Plains/Tarrytown

8/10 Good

"The property is situated in a good location. The room was nice and clean. The beds were comfortable, and breakfast was good. There is also a diner nearby. The issue at this property is the parking. It is broken up into weird little lots with tight parking spaces. There were inconsiderate guests splitting the spots and taking multiple spots for their one vehicle. Other than the parking, I would recommend and stay here again."

Find out more about Ossining

Everything you need to know about Ossining vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ossining vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ossining vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ossining vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ossining. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Ossining in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $177 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ossining rentals

At Expedia, we put the best Ossining vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ossining rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ossining vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ossining. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Things to do in Nyack

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. Ossining Public Library 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.

Ossining Vacation Rentals

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Check prices for these dates

Our top choices for Ossining vacation rentals

1. NYC-Area Escape Near River, Trails & MTA!

2. Nyc-area Escape Near River, Trails & Mta!

3. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

4. Summer Pool Oasis Custom Bar Arcade Pool Table

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

6. Polished 1BR w/ Accessible Room Features + Sauna

7. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

8. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

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

10. Piermont Oasis

11. 1 Queen Bed | Smoking

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

13. House on the Babbling Brook- Quiet 2BR + King Bed!

14. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

15. Contemporary Cozy Cottage

16. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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

18. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

19. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

20. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Find vacation rentals that suit your style

Top Ossining Hotel Reviews

LIV Hotel Bronx - Newly Built

Find out more about Ossining

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