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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Pound Ridge cottages

Property grounds

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

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
The price is AU$1,072
includes taxes & fees
18 Aug - 19 Aug
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
House (5 Bedrooms) | Interior

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
3 Mi to Downtown: Spacious White Plains Home
Exterior

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is AU$937
includes taxes & fees
1 Aug - 2 Aug
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Property grounds

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, (7 reviews)
"This house is the perfect private getaway! Everything was just as described and the host was super helpful. Will definitely stay again. "
United States
Anna F.
The price is AU$1,778
includes taxes & fees
9 Aug - 10 Aug
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
House (4 Bedrooms) | Interior

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$934
includes taxes & fees
2 Aug - 3 Aug
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

The Watershed

The Watershed

10/10 Excellent
"We loved our stay there! It was close to Fairfield University. We stayed for our daughter’s orientation date and it was comfortable, clean, and a quick drive to the university. We will definitely be back for future stays when visiting."
Suzanne 1-night trip
Posted 1 hour ago
The Watershed

Find out more about Pound Ridge

Pound Ridge Cottages information

Number of reviews
36
Accommodation
65 Cottages
Lowest Price
AU$934
Highest Price
AU$1,778

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.