We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Ossining

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
50 rentals in Ossining.
Cozy house on the Hudson, holiday rental in Ossining
Cozy house on the Hudson, holiday rental in Ossining
Cozy house on the Hudson, holiday rental in Ossining

Cozy house on the Hudson

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Camped Inn at Sundial Farm -- Tiny House, holiday rental in Ossining
Camped Inn at Sundial Farm -- Tiny House, holiday rental in Ossining
Camped Inn at Sundial Farm -- Tiny House, holiday rental in Ossining

Camped Inn at Sundial Farm -- Tiny House

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Lovely one bedroom apartment in Westchester, NY!, holiday rental in Ossining
Lovely one bedroom apartment in Westchester, NY!, holiday rental in Ossining
Lovely one bedroom apartment in Westchester, NY!, holiday rental in Ossining

Lovely one bedroom apartment in Westchester, NY!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Hudson River Peaceful Getaway, holiday rental in Ossining
Hudson River Peaceful Getaway, holiday rental in Ossining
Hudson River Peaceful Getaway, holiday rental in Ossining

Hudson River Peaceful Getaway

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Neighbor's house - Welcome!, holiday rental in Ossining
Neighbor's house - Welcome!, holiday rental in Ossining
Neighbor's house - Welcome!, holiday rental in Ossining

Neighbor's house - Welcome!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
1920's Home with some river views close to NYC, holiday rental in Ossining
1920's Home with some river views close to NYC, holiday rental in Ossining
1920's Home with some river views close to NYC, holiday rental in Ossining

1920's Home with some river views close to NYC

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
The following properties within 32 kms of Ossining match all your filters:
The Perfect Studio Getaway, holiday rental in Ossining
The Perfect Studio Getaway, holiday rental in Ossining
The Perfect Studio Getaway, holiday rental in Ossining

The Perfect Studio Getaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Charming 1 Bedroom in the middle of downtown Nyack, holiday rental in Ossining
Charming 1 Bedroom in the middle of downtown Nyack, holiday rental in Ossining
Charming 1 Bedroom in the middle of downtown Nyack, holiday rental in Ossining

Charming 1 Bedroom in the middle of downtown Nyack

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Hudson Valley Getaway for Families, holiday rental in Ossining
Hudson Valley Getaway for Families, holiday rental in Ossining
Hudson Valley Getaway for Families, holiday rental in Ossining

Hudson Valley Getaway for Families

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Brand new private Studio in the heart of Tarrytown, holiday rental in Ossining
Brand new private Studio in the heart of Tarrytown, holiday rental in Ossining
Brand new private Studio in the heart of Tarrytown, holiday rental in Ossining

Brand new private Studio in the heart of Tarrytown

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
River front with large decks and dock over the Hudson, holiday rental in Ossining
River front with large decks and dock over the Hudson, holiday rental in Ossining
River front with large decks and dock over the Hudson, holiday rental in Ossining

River front with large decks and dock over the Hudson

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Duplex WATERFRONT HOME, holiday rental in Ossining
Duplex WATERFRONT HOME, holiday rental in Ossining
Duplex WATERFRONT HOME, holiday rental in Ossining

Duplex WATERFRONT HOME

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Luxury home filled with books and art, with great access. Sleeps up to fourteen., holiday rental in Ossining
Luxury home filled with books and art, with great access. Sleeps up to fourteen., holiday rental in Ossining
Luxury home filled with books and art, with great access. Sleeps up to fourteen., holiday rental in Ossining

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
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food, holiday rental in Ossining
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food, holiday rental in Ossining
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food, holiday rental in Ossining

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Piermont Cozy Haven, holiday rental in Ossining
Piermont Cozy Haven, holiday rental in Ossining
Piermont Cozy Haven, holiday rental in Ossining

Piermont Cozy Haven

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Cozy Cottage Get Away, holiday rental in Ossining
Cozy Cottage Get Away, holiday rental in Ossining
Cozy Cottage Get Away, holiday rental in Ossining

Cozy Cottage Get Away

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Gorgeous Boat - weekend on the water -  2 bdrm Cabin Cruiser-yacht club included, holiday rental in Ossining
Gorgeous Boat - weekend on the water -  2 bdrm Cabin Cruiser-yacht club included, holiday rental in Ossining
Gorgeous Boat - weekend on the water -  2 bdrm Cabin Cruiser-yacht club included, holiday rental in Ossining

Gorgeous Boat - weekend on the water - 2 bdrm Cabin Cruiser-yacht club included

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Cozy 2 Bedroom 1 bath, walking dustance from all the fun!, holiday rental in Ossining
Cozy 2 Bedroom 1 bath, walking dustance from all the fun!, holiday rental in Ossining
Cozy 2 Bedroom 1 bath, walking dustance from all the fun!, holiday rental in Ossining

Cozy 2 Bedroom 1 bath, walking dustance from all the fun!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Need a place to relax and enjoy your vacation stay at The Cozy Den, holiday rental in Ossining
Need a place to relax and enjoy your vacation stay at The Cozy Den, holiday rental in Ossining
Need a place to relax and enjoy your vacation stay at The Cozy Den, holiday rental in Ossining

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
More info
Check-in
Check-out
As seen on
Vrbo.com logo
2BDRM COTTAGE IN PLEASANTVILLE, holiday rental in Ossining
2BDRM COTTAGE IN PLEASANTVILLE, holiday rental in Ossining
2BDRM COTTAGE IN PLEASANTVILLE, holiday rental in Ossining

2BDRM COTTAGE IN PLEASANTVILLE

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Lovely cottage, ideal location, holiday rental in Ossining
Lovely cottage, ideal location, holiday rental in Ossining
Lovely cottage, ideal location, holiday rental in Ossining

Lovely cottage, ideal location

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Beautiful Brand New  Private Duplex Unit in  Lower Hudson Valley  "Stone Haven", holiday rental in Ossining
Beautiful Brand New  Private Duplex Unit in  Lower Hudson Valley  "Stone Haven", holiday rental in Ossining
Beautiful Brand New  Private Duplex Unit in  Lower Hudson Valley  "Stone Haven", holiday rental in Ossining

Beautiful Brand New Private Duplex Unit in Lower Hudson Valley "Stone Haven"

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Luxury Hudson River Retreat- quaint town, nature & NYC nearby., holiday rental in Ossining
Luxury Hudson River Retreat- quaint town, nature & NYC nearby., holiday rental in Ossining
Luxury Hudson River Retreat- quaint town, nature & NYC nearby., holiday rental in Ossining

Luxury Hudson River Retreat- quaint town, nature & NYC nearby.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Enjoy the best of both worlds, holiday rental in Ossining
Enjoy the best of both worlds, holiday rental in Ossining
Enjoy the best of both worlds, holiday rental in Ossining

Enjoy the best of both worlds

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Charming Elmsford Home ~ 23 Mi to Manhattan!, holiday rental in Ossining
Charming Elmsford Home ~ 23 Mi to Manhattan!, holiday rental in Ossining
Charming Elmsford Home ~ 23 Mi to Manhattan!, holiday rental in Ossining

Charming Elmsford Home ~ 23 Mi to Manhattan!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Tranquil Country Contemporary, holiday rental in Ossining
Tranquil Country Contemporary, holiday rental in Ossining
Tranquil Country Contemporary, holiday rental in Ossining

Tranquil Country Contemporary

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Riverhouse- 1 Hr From Nyc- 2br /deck/ Hike/bike Trail/canoe/kyack, holiday rental in Ossining
Riverhouse- 1 Hr From Nyc- 2br /deck/ Hike/bike Trail/canoe/kyack, holiday rental in Ossining
Riverhouse- 1 Hr From Nyc- 2br /deck/ Hike/bike Trail/canoe/kyack, holiday rental in Ossining

Riverhouse- 1 Hr From Nyc- 2br /deck/ Hike/bike Trail/canoe/kyack

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Cozy home overlooking the water with a great view of the Tappan Zee Bridge., holiday rental in Ossining
Cozy home overlooking the water with a great view of the Tappan Zee Bridge., holiday rental in Ossining
Cozy home overlooking the water with a great view of the Tappan Zee Bridge., holiday rental in Ossining

Cozy home overlooking the water with a great view of the Tappan Zee Bridge.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Stay in Nyack, walking distance from village center, holiday rental in Ossining
Stay in Nyack, walking distance from village center, holiday rental in Ossining
Stay in Nyack, walking distance from village center, holiday rental in Ossining

Stay in Nyack, walking distance from village center

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Historic Chateau Marmot on the Hudson, holiday rental in Ossining
Historic Chateau Marmot on the Hudson, holiday rental in Ossining
Historic Chateau Marmot on the Hudson, holiday rental in Ossining

Historic Chateau Marmot on the Hudson

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Victorian Farmhouse with Pool near NYC, holiday rental in Ossining
Victorian Farmhouse with Pool near NYC, holiday rental in Ossining
Victorian Farmhouse with Pool near NYC, holiday rental in Ossining

Victorian Farmhouse with Pool near NYC

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Historic cottage with majestic river views, holiday rental in Ossining
Historic cottage with majestic river views, holiday rental in Ossining
Historic cottage with majestic river views, holiday rental in Ossining

Historic cottage with majestic river views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Private Pool Oasis just 50 minutes outside of Manhattan!, holiday rental in Ossining
Private Pool Oasis just 50 minutes outside of Manhattan!, holiday rental in Ossining
Private Pool Oasis just 50 minutes outside of Manhattan!, holiday rental in Ossining

Private Pool Oasis just 50 minutes outside of Manhattan!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Beautiful Private House; Golf, Hike, Fish, Swim, Relax, holiday rental in Ossining
Beautiful Private House; Golf, Hike, Fish, Swim, Relax, holiday rental in Ossining
Beautiful Private House; Golf, Hike, Fish, Swim, Relax, holiday rental in Ossining

Beautiful Private House; Golf, Hike, Fish, Swim, Relax

Holiday Rental House
2 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Holiday cozy country cottage!, holiday rental in Ossining
Holiday cozy country cottage!, holiday rental in Ossining
Holiday cozy country cottage!, holiday rental in Ossining

Holiday cozy country cottage!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
The Best of Both Worlds: For nature lovers but close to New York City, holiday rental in Ossining
The Best of Both Worlds: For nature lovers but close to New York City, holiday rental in Ossining
The Best of Both Worlds: For nature lovers but close to New York City, holiday rental in Ossining

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
More info
Check-in
Check-out
As seen on
Vrbo.com logo
The Red Hill Retreat - Woods Water History Privacy, holiday rental in Ossining
The Red Hill Retreat - Woods Water History Privacy, holiday rental in Ossining
The Red Hill Retreat - Woods Water History Privacy, holiday rental in Ossining

The Red Hill Retreat - Woods Water History Privacy

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Relaxing & Great Location & Minutes from New York, holiday rental in Ossining
Relaxing & Great Location & Minutes from New York, holiday rental in Ossining
Relaxing & Great Location & Minutes from New York, holiday rental in Ossining

Relaxing & Great Location & Minutes from New York

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Family home in one of NY top-ranked school districts with Tennis court, holiday rental in Ossining
Family home in one of NY top-ranked school districts with Tennis court, holiday rental in Ossining
Family home in one of NY top-ranked school districts with Tennis court, holiday rental in Ossining

Family home in one of NY top-ranked school districts with Tennis court

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Luxury Home + XL Pool near NYC/Harriman State Park, holiday rental in Ossining
Luxury Home + XL Pool near NYC/Harriman State Park, holiday rental in Ossining
Luxury Home + XL Pool near NYC/Harriman State Park, holiday rental in Ossining

Luxury Home + XL Pool near NYC/Harriman State Park

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 25
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Briarcliff Manor Estate w/ Hudson River Views, holiday rental in Ossining
Briarcliff Manor Estate w/ Hudson River Views, holiday rental in Ossining
Briarcliff Manor Estate w/ Hudson River Views, holiday rental in Ossining

Briarcliff Manor Estate w/ Hudson River Views

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Private Chic Modern Farmhouse Pool, HotTub, pool table, Sunsets, 6BR, Offices, holiday rental in Ossining
Private Chic Modern Farmhouse Pool, HotTub, pool table, Sunsets, 6BR, Offices, holiday rental in Ossining
Private Chic Modern Farmhouse Pool, HotTub, pool table, Sunsets, 6BR, Offices, holiday rental in Ossining

Private Chic Modern Farmhouse Pool, HotTub, pool table, Sunsets, 6BR, Offices

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Modern Mansion Near NYC, Airports, Restaurants, Activities, Shopping & More!, holiday rental in Ossining
Modern Mansion Near NYC, Airports, Restaurants, Activities, Shopping & More!, holiday rental in Ossining
Modern Mansion Near NYC, Airports, Restaurants, Activities, Shopping & More!, holiday rental in Ossining

Modern Mansion Near NYC, Airports, Restaurants, Activities, Shopping & More!

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Favorite Holiday Country Estate for Gathering with Family, Friends, Corporate., holiday rental in Ossining
Favorite Holiday Country Estate for Gathering with Family, Friends, Corporate., holiday rental in Ossining
Favorite Holiday Country Estate for Gathering with Family, Friends, Corporate., holiday rental in Ossining

Favorite Holiday Country Estate for Gathering with Family, Friends, Corporate.

Holiday Rental House
9 bedrooms
8 bathrooms
Sleeps 26
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
2 bedroom apartment in Tarrytown/Sleepy Hollow, holiday rental in Ossining
2 bedroom apartment in Tarrytown/Sleepy Hollow, holiday rental in Ossining
2 bedroom apartment in Tarrytown/Sleepy Hollow, holiday rental in Ossining

2 bedroom apartment in Tarrytown/Sleepy Hollow

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Cozy Lake House just an hour from NYC!, holiday rental in Ossining
Cozy Lake House just an hour from NYC!, holiday rental in Ossining
Cozy Lake House just an hour from NYC!, holiday rental in Ossining

Cozy Lake House just an hour from NYC!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Stone Manor, holiday rental in Ossining
Stone Manor, holiday rental in Ossining
Stone Manor, holiday rental in Ossining

Stone Manor

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Luxury 8 BR Estate with Pool and Tennis court, holiday rental in Ossining
Luxury 8 BR Estate with Pool and Tennis court, holiday rental in Ossining
Luxury 8 BR Estate with Pool and Tennis court, holiday rental in Ossining

Luxury 8 BR Estate with Pool and Tennis court

Holiday Rental House
8 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Private room in a single family house near Peekskill, holiday rental in Ossining
Private room in a single family house near Peekskill, holiday rental in Ossining
Private room in a single family house near Peekskill, holiday rental in Ossining

Private room in a single family house near Peekskill

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Charming Retreat w/ Fire Pit & Spacious Yard!, holiday rental in Ossining
Charming Retreat w/ Fire Pit & Spacious Yard!, holiday rental in Ossining
Charming Retreat w/ Fire Pit & Spacious Yard!, holiday rental in Ossining

Charming Retreat w/ Fire Pit & Spacious Yard!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Showing results 1-50 of 50
Frequently Asked Questions about Ossining