Ossining Vacation Rentals
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5 mi
48 rentals in Ossining.
Cozy house on the Hudson
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Camped Inn at Sundial Farm -- Tiny House
Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Lovely one bedroom apartment in Westchester, NY!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Hudson River Peaceful Getaway
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Neighbor's house - Welcome!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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The following properties within 20 miles of Ossining match all your filters:
Hudson Valley Getaway for Families
Rental Home
6 bedrooms
3 bathrooms
Sleeps 12
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Brand new private Studio in the heart of Tarrytown
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
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Updated Getaway w/ Pool & Hot Tub on 2.5 Acres!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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River front with large decks and dock over the Hudson
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
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Duplex WATERFRONT HOME
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Nature's Paradise
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Piermont Cozy Haven
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Stay into a private room.
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Peekskill Guesthouse- PrivateRoom Downtown KingBed Hotel Amenities EpicViews
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Cottage Get Away
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Peekskill Carriage House Downtown Studio
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Gorgeous Boat - weekend on the water - 2 bdrm Cabin Cruiser-yacht club included
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Cozy 2 Bedroom 1 bath, walking dustance from all the fun!
Rental Home
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
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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2BDRM COTTAGE IN PLEASANTVILLE
Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
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Bright&Comfy 2bed/1ba in quiet White Plains duplex
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Lovely cottage, ideal location
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Luxury Hudson River Retreat- quaint town, nature & NYC nearby.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 2
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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!
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Tranquil Country Contemporary
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Riverhouse- 1 Hr From Nyc- 2br /deck/ Hike/bike Trail/canoe/kyack
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Modern charming country cottage for long term availability
Rental Home
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Stay in Nyack, walking distance from village center
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Historic Chateau Marmot on the Hudson
Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
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DOMIR Yorktown
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Pool Oasis just 50 minutes outside of Manhattan!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Private House; Golf, Hike, Fish, Swim, Relax
Rental Home
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
Rental Home
4 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Luxury in Town
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Red Hill Retreat - Woods Water History Privacy
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Gracious Country Home
Rental Home
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
Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
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A spectacular contemporary home sits in downtown historic Piermont
Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Modern Mansion Near NYC, Airports, Restaurants, Activities, Shopping & More!
Rental Home
6 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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19th century castle with modern amenities
Rental Home
9 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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Luxury 8 BR Estate with Pool and Tennis court
Rental Home
8 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
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Stone Manor
Rental Home
4 bedrooms
6 bathrooms
Sleeps 10
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Astonishing 1852 Italianate Villa Nuits estate. 30 minutes from midtown NYC.
Rental Home
10 bedrooms
10 bathrooms
Sleeps 24
Match: Sleeps
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Charming Retreat w/ Fire Pit & Spacious Yard!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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Cozy Lake House just an hour from NYC!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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Showing results 1-48 of 48
Frequently Asked Questions about Ossining
- Yes, here are some popular vacation 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 vacation 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 vacation rentals in Ossining on Tripadvisor
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