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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Pound Ridge cottages

A wooden deck with a railing overlooking a well-maintained lawn and trees.

1. 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.
$584 nightly
The price is $669
Nov 29 - Nov 30
Total with taxes and fees
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
A two-story house with a wooden exterior, a front porch, and a staircase leading to the entrance.

2. 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
$472 nightly
The price is $521
Nov 15 - Nov 16
Total with taxes and fees
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A two-story house with a white picket fence, a garage, and a tree in front.

3. Nama-stay, sweet pink Saugatuck Shores beach cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.4 out of 10, Exceptional, (19 reviews)
"A sweet get away for which the highlights included a breezy screened porch and sensational walks right from the property. Easy shopping and neighbors right out of central casting who provided additional restaurant suggestions and general warmth. Would stay here again in a heart beat. We were here for a week and were sad to leave."
United States
Mel O.
$387 nightly
The price is $441
Nov 15 - Nov 16
Total with taxes and fees
Nama-stay, sweet pink Saugatuck Shores beach cottage
A deck with wicker furniture overlooking a river.

4. Historic, private riverfront cottage in peaceful Greenwich

Historic, private riverfront cottage in peaceful Greenwich
Greenwich
$318 nightly
The price is $362
Nov 23 - Nov 24
Total with taxes and fees
Historic, private riverfront cottage in peaceful Greenwich
A wooden deck with a railing overlooking a body of water and trees.

5. 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.
$353 nightly
The price is $404
Nov 15 - Nov 16
Total with taxes and fees
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A wooden house with a stone pathway leading to a wooden deck.

6. 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.
$1,347 nightly
The price is $1,533
Nov 15 - Nov 16
Total with taxes and fees
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
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 Pound Ridge

Hikers discover miles of scenic trails through the Pound Ridge Reservation, where forest paths lead to peaceful streams and rocky outcroppings. Families gather at the Ward Pound Ridge Museum to explore local history before picnicking in the meadows nearby.

See all hotels in Pound Ridge
A stone dam with a waterfall, a bridge, and a forested hillside.

Top reviews in Pound Ridge

A wooden interior with a reception desk, framed botanical prints, and a sign reading "The Water."
The Watershed

The Watershed

The Watershed
Cranbury

10/10 Excellent

Beautiful hotel! We would definitely stay again.
United States
Donna
Reviewed June 24, 2025
The Watershed

Frequently Asked Questions

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