Ossining Holiday Rentals
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Distinctive Features
Distance from
5 mi
50 rentals in Ossining.
Cozy house on the Hudson
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Camped Inn at Sundial Farm -- Tiny House
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lovely one bedroom apartment in Westchester, NY!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hudson River Peaceful Getaway
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Neighbor's house - Welcome!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The following properties within 20 miles of Ossining match all your filters:
The Perfect Studio Getaway
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Affiliated with FlipKey
Hudson Valley Getaway for Families
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Brand new private Studio in the heart of Tarrytown
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Updated Getaway w/ Pool & Hot Tub on 2.5 Acres!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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DOMIR Yorktown stay
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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River front with large decks and dock over the Hudson
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Duplex WATERFRONT HOME
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury home filled with books and art, with great access. Sleeps up to fourteen.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Nature's Paradise
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Piermont Cozy Haven
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stay into a private room.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Peekskill Guesthouse- PrivateRoom Downtown KingBed Hotel Amenities EpicViews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Cottage Get Away
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Peekskill Carriage House Downtown Studio
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Gorgeous Boat - weekend on the water - 2 bdrm Cabin Cruiser-yacht club included
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy 2 Bedroom 1 bath, walking dustance from all the fun!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Need a place to relax and enjoy your vacation stay at The Cozy Den
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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2BDRM COTTAGE IN PLEASANTVILLE
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Lovely cottage, ideal location
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury Hudson River Retreat- quaint town, nature & NYC nearby.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Enjoy the best of both worlds
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Charming Elmsford Home ~ 23 Mi to Manhattan!
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Tranquil Country Contemporary
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Riverhouse- 1 Hr From Nyc- 2br /deck/ Hike/bike Trail/canoe/kyack
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Modern charming country cottage for long term availability
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Stay in Nyack, walking distance from village center
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Historic Chateau Marmot on the Hudson
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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DOMIR Yorktown
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Pool Oasis just 50 minutes outside of Manhattan!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Private House; Golf, Hike, Fish, Swim, Relax
Holiday Rental House
2 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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The Best of Both Worlds: For nature lovers but close to New York City
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Luxury in Town
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Red Hill Retreat - Woods Water History Privacy
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Gracious Country Home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Family home in one of NY top-ranked school districts with Tennis court
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Briarcliff Manor Estate w/ Hudson River Views
Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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A spectacular contemporary home sits in downtown historic Piermont
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Modern Mansion Near NYC, Airports, Restaurants, Activities, Shopping & More!
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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19th century castle with modern amenities
Holiday Rental House
9 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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2 bedroom apartment in Tarrytown/Sleepy Hollow
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury 8 BR Estate with Pool and Tennis court
Holiday Rental House
8 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
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Cozy Lake House just an hour from NYC!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Stone Manor
Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Charming Retreat w/ Fire Pit & Spacious Yard!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Showing results 1-50 of 50
Frequently Asked Questions about Ossining
- Yes, here are some popular holiday rentals in Ossining that have a pool:
- Cozy house on the Hudson
- Camped Inn at Sundial Farm -- Tiny House
- Lovely one bedroom apartment in Westchester, NY!
- Yes, here are some popular holiday rentals in Ossining that have internet access:
- Cozy house on the Hudson
- Camped Inn at Sundial Farm -- Tiny House
- Lovely one bedroom apartment in Westchester, NY!
- The best pet friendly rentals in Ossining are:
- Cozy house on the Hudson
- Camped Inn at Sundial Farm -- Tiny House
- Lovely one bedroom apartment in Westchester, NY!
- Some of the most popular kid friendly rentals in Ossining are:See all kid friendly holiday rentals in Ossining on Tripadvisor
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