Search Vacation Homes in Pound Ridge

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Our top choices for Pound Ridge vacation homes

9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
$172 nightly
The price is $195
Dec 14 - Dec 15
Total with taxes and fees
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
2.0 star property
9.6 out of 10, Exceptional, (4)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
$479 nightly
The price is $541
Dec 22 - Dec 23
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
9.8 out of 10, Exceptional, (8)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
$348 nightly
The price is $394
Dec 15 - Dec 16
Total with taxes and fees
Marine Theme - 4 BR - Backyard - Fire pit
9.6 out of 10, Exceptional, (23)
"The property was beautiful and clean, very comfortable with a nice view of the lake! Our hosts were helpful and attentive without being intrusive in any way. Our stay was peaceful and restful, just perfect. "
United States
Victoria R.
$228 nightly
The price is $258
Dec 15 - Dec 16
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
$328 nightly
The price is $355
Dec 15 - Dec 16
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Vacation Home in Brooklawn - St. Vincent

Centric property close to all the great things in the city
7.2 out of 10, Good, (13)
"This rental was great accommodation"
United States
Alma B.
$263 nightly
The price is $297
Dec 14 - Dec 15
Total with taxes and fees
Centric property close to all the great things in the city
10.0 out of 10, Exceptional, (11)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
$433 nightly
The price is $501
Dec 15 - Dec 16
Total with taxes and fees
Bright Escape, Top-Rated Design, Fire pit, Near Beach
9.8 out of 10, Exceptional, (9)
"Lovely little home in Stamford."
United States
Pat A.
$291 nightly
The price is $329
Dec 16 - Dec 17
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
10.0 out of 10, Exceptional, (22)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
$424 nightly
The price is $480
Jan 12 - Jan 13, 2026
Total with taxes and fees
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
10.0 out of 10, Exceptional, (16)
"The house worked very well for our family holiday. Very clean, had everything we needed "
United States
Audrey P.
$466 nightly
The price is $528
Dec 17 - Dec 18
Total with taxes and fees
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
9.4 out of 10, Exceptional, (6)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
United States
April R.
$1,403 nightly
The price is $1,587
Dec 14 - Dec 15
Total with taxes and fees
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Vacation Home in Brooklawn - St. Vincent

The B&W Haven 5BR Home with yard theater + Office
9.4 out of 10, Exceptional, (8)
"Host was very polite and communicated well throughout the stay. The property appears well maintained. There are window units but everyone was comfortable for the duration of our stay."
United States
George M.
$593 nightly
The price is $672
Dec 15 - Dec 16
Total with taxes and fees
The B&W Haven 5BR Home with yard theater + Office

Vacation Home in North End

Beechmont - Perfect for Family Retreat!
5.0 star property
$1,151 nightly
The price is $1,323
Dec 14 - Dec 15
Total with taxes and fees
Beechmont - Perfect for Family Retreat!

Vacation Home in West End - West Side

Modern + Spacious 5BR/2BA Home, Renovated Backyard
9.6 out of 10, Exceptional, (4)
"Used for family weekend at SHU. Convenient location and plenty of space for the whole family! "
United States
Laurene S.
$682 nightly
The price is $773
Dec 14 - Dec 15
Total with taxes and fees
Modern + Spacious 5BR/2BA Home, Renovated Backyard
10.0 out of 10, Exceptional, (1)
"The Host was welcoming and responsive to our inquiries!Our stay was wonderful! The property was spectacular and offered all the amenities we needed for a comfortable and enjoyable visit. "
United States
Patricia B.
$1,631 nightly
The price is $1,849
Dec 14 - Dec 15
Total with taxes and fees
🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna

Vacation Home in Lake Peekskill

Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
$395 nightly
The price is $452
Dec 29 - Dec 30
Total with taxes and fees
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (2)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
$525 nightly
The price is $599
Dec 17 - Dec 18
Total with taxes and fees
Country Retreat | Heated Saltwater Pool | BBQ | Fire Pit
2.0 star property
10.0 out of 10, Exceptional, (8)
"We were so pleased with the accommodations. The location is so quiet in a charming neighborhood. The home is well equipped with kitchen supplied and entertainment options. We were delighted to be able to barbecue. Claudia is very responsive and helpful."
Canada
nawab k.
$475 nightly
The price is $538
Dec 14 - Dec 15
Total with taxes and fees
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
10.0 out of 10, Exceptional, (21)
"Our hosts were very attentive and responsive with communications. The house is lovely, clean, well stocked and in a great location. We thoroughly enjoyed our stay!"
United States
Megan P.
$354 nightly
The price is $401
Jan 5 - Jan 6, 2026
Total with taxes and fees
45 Minutes from NYC, Entire House near Stamford Downtown,

Vacation Home in North Stamford

Bright Stylish Chic 4BR 4BA Home Pet Friendly!
10.0 out of 10, Exceptional, (105)
"Wonderful family home!Everything you need!Beautiful location!Great host!"
United States
Linda T.
$811 nightly
The price is $918
Dec 14 - Dec 15
Total with taxes and fees
Bright Stylish Chic 4BR 4BA Home 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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Top Pound Ridge Hotel Reviews

Find out more about Pound Ridge

Pound Ridge Vacation Homes information

Number of reviews
287
Accommodation
361 Vacation Homes
Lowest Price
$195
Highest Price
$1,849

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