A serene park with a pond, a small boat, and autumn-colored trees.

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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)
"lovely porch and backyard."
United States
Kaia W.
The price is AU$1,051
includes taxes & fees
11 Nov - 12 Nov
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
A wooden house with a stone pathway leading to a wooden deck.

2. 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, (13 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is AU$2,201
includes taxes & fees
3 Nov - 4 Nov
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
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)
"Great fenced in yard for our pup"
United States
Deb S.
The price is AU$645
includes taxes & fees
11 Nov - 12 Nov
Nama-stay, sweet pink Saugatuck Shores beach cottage
A wooden deck with a railing overlooking a body of water and trees.

4. 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, (27 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is AU$583
includes taxes & fees
9 Nov - 10 Nov
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A two-story house with a white picket fence, a front porch, and a visible staircase leading to the entrance.

5. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is AU$1,315
includes taxes & fees
28 Oct - 29 Oct
4 Mi to Beach & Dtwn! Charming Fairfield Home
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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Top Pound Ridge Hotel Reviews

Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham

10/10 Excellent
"Too Expensive breakfast, long walk to rooms"
Cheryl 3-night trip
Posted 11 hours ago
Sleepy Hollow Hotel, a Dolce by Wyndham

Find out more about Pound Ridge

Pound Ridge Cottages information

Number of reviews
57
Accommodation
69 Cottages
Lowest Price
AU$583
Highest Price
AU$2,201

Frequently asked questions

What is there to do in Pound Ridge near my cottage?
Pound Ridge has enough sights and experiences to keep you busy for weeks (or months!), starting with Ridgefield Playhouse. Wolf Conservation Centre, Wilton Historical Society and Muscoot Farm are other impressive attractions. If you have more time, Stamford Historical Society Museum and Katonah Museum of Art are worthwhile additions to your itinerary.