Sleepy Hollow Cottages

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Cottages in Sleepy Hollow

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery NY

$277 nightly

$327 total

Jun 17 - Jun 18

Total with taxes and fees

When you stay at this cottage in Fort Montgomery, you'll be on a river, within a 15-minute drive of Bear Mountain State Park and United States Military Academy.

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

Greenwich CT

$1,191 nightly

$1,350 total

Jun 19 - Jun 20

Total with taxes and fees

With a stay at this cottage in Greenwich, you'll be within a 15-minute drive of Greenwich Avenue and Rye Playland.

Lovely Home Near FDU & Holy Name Hospital!

Teaneck NJ

Located in Teaneck, this cottage is within a 15-minute drive of American Dream and Yankee Stadium.

Summer fun on the river. Swim, fish, kayak and bird watch at Croton River Gorge.

Croton-on-Hudson NY

Located in Croton-on-Hudson, this cottage is a 3-minute drive from Van Cortlandt Manor and 6 minutes from Brinton Brook Sanctuary.

Stylish Loft with Parking Near NYC + Hospital

Stamford CT

With a stay at this cottage, you'll be centrally located in Stamford, within a 10-minute drive of Greenwich Avenue and E. Gaynor Brennan Golf Course.

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Putnam Valley NY

Located in Lake Peekskill, this cottage is within a 15-minute drive of Hudson Valley Center for Contemporary Art and Oscawana Lake.

Second floor cottage apartment located in a private community.

Stamford CT

With a stay at this cottage in Stamford (Cove - East Side - Shippan), you'll be within a 15-minute drive of Greenwich Avenue and Cummings Park.

3 Mi to Downtown: Spacious White Plains Home

White Plains NY

With a stay at this cottage in White Plains, you'll be within a 5-minute drive of Westchester County Center and Greenburgh Public Library.

Cos Cob Cottage- Full Kitchen, Pet Friendly

Greenwich CT

With a stay at this cottage in Cos Cob, you'll be within a 5-minute drive of Greenwich Avenue and Bible Street Playground.

'the Glabin: Garrison Gem w/ Hot Tub & Fire Pit

Garrison NY

Located in Philipstown, this cottage is a 4-minute drive from Graymoor - The Holy Mountain and 9 minutes from Lincoln Depot Museum.

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

Pound Ridge NY

Located in Pound Ridge, this cottage is in a rural location, within a 15-minute drive of New Canaan Museum & Historical Society and New Canaan Town Hall.

Charming Highland Falls Home < 2 Mi to West Point!

Highland Falls NY

With a stay at this cottage in Highland Falls, you'll be a 2-minute drive from Bear Mountain State Park and 6 minutes from United States Military Academy.

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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.