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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Pleasantville cottages

A wooden deck with a railing overlooking a body of water and trees.

1. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (28 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is CA $350
CA $566 total
includes taxes & fees
Dec 8 - Dec 9
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A deck with wicker furniture overlooking a river.

2. Historic, private riverfront cottage in peaceful Greenwich

Historic, private riverfront cottage in peaceful Greenwich
Greenwich
The price is CA $315
CA $511 total
includes taxes & fees
Dec 8 - Dec 9
Historic, private riverfront cottage in peaceful Greenwich
A wooden house with a stone pathway leading to a wooden deck.

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

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Greenwich
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is CA $1,138
CA $2,078 total
includes taxes & fees
Nov 8 - Nov 9
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
A two-story house with a wooden exterior, a front porch, and a staircase leading to the entrance.

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

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (25 reviews)
"Absolute comfortable stay. Everything you need and fantastic host!! Will be back."
United States
Lisa
The price is CA $408
CA $879 total
includes taxes & fees
Nov 13 - Nov 14
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A wooden deck with a railing overlooking a well-maintained lawn and trees.

5. Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
9.8 out of 10, Exceptional, (11 reviews)
"Beautiful setting, and plenty of room for a family of four. Accommodations were very clean and spacious. Thank you for hosting us!"
United States
Susan K.
The price is CA $444
CA $984 total
includes taxes & fees
Nov 29 - Nov 30
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
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.
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Learn more about Pleasantville

This charming Westchester village offers a peaceful escape with its walkable downtown filled with independent shops and the Jacob Burns Film Centre. Grab a coffee at The Black Cow before exploring nearby Rockefeller State Park Preserve's scenic trails and stone bridges.

See all hotels in Pleasantville
A calm lake surrounded by autumn-colored trees reflecting in the water.

Top reviews in Pleasantville

A Holiday Inn Express & Suites hotel with a modern design, featuring a covered entrance and American flags.
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Hawthorne

10/10 Excellent

Room and all around the hotel was cleaned and kept clean throughout my stay. Staff were VERY welcoming and helpful and the free breakfast was a bonus & I can’t forget about their 24hr coffee machine, it is definitely worth the entire stay.
Canada
Kiarra
Reviewed August 6, 2026
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

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