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Our top choices for Pound Ridge vacation homes

1. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (46 reviews)
"Nice stay"
United States
Christopher J.
The price is AED 630
AED 1,184 total
includes taxes & fees
15 Nov - 16 Nov
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is AED 819
AED 1,487 total
includes taxes & fees
18 Nov - 19 Nov
Gilded Age Luxury Surrounded by Nature

3. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
8.6 out of 10, Excellent, (4 reviews)
"We had a wonderful stay."
United States
Linda S.
The price is AED 1,299
AED 2,769 total
includes taxes & fees
18 Nov - 19 Nov
Spacious Retreat with Game Room and Fire Pit

4. Gem by the water+ firepit and all fenced backyard

Gem by the water+ firepit and all fenced backyard
Waterside
10.0 out of 10, Exceptional, (22 reviews)
"Property was exactly what we needed for our stay"
United States
Christopher E.
The price is AED 824
AED 1,633 total
includes taxes & fees
17 Nov - 18 Nov
Gem by the water+ firepit and all fenced backyard

5. 3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ

3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ
Cranbury
8.8 out of 10, Excellent, (8 reviews)
"Great spot for our family. "
United States
Kevin I.
The price is AED 1,084
AED 2,150 total
includes taxes & fees
19 Nov - 20 Nov
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ

6. Spacious 3BR Townhome | Garage + Near Downtown

Spacious 3BR Townhome | Garage + Near Downtown
West Side
9.2 out of 10, Wonderful, (9 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is AED 1,010
AED 2,005 total
includes taxes & fees
16 Nov - 17 Nov
Spacious 3BR Townhome | Garage + Near Downtown

7. Spacious 3BR | Family + Work | Ample Parking

Spacious 3BR | Family + Work | Ample Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"Great location - very spacious and strong AC! host was very communicative and easy to deal with."
United States
Cari B.
The price is AED 852
AED 1,707 total
includes taxes & fees
15 Nov - 16 Nov
Spacious 3BR | Family + Work | Ample Parking

8. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (16 reviews)
"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."
United States
Melissa H.
The price is AED 856
AED 2,215 total
includes taxes & fees
15 Nov - 16 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

9. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is AED 1,101
AED 2,541 total
includes taxes & fees
18 Nov - 19 Nov
Renovated Retreat with Heated Pool

10. 5BR Water View Home, Sauna, Game Room, Fire Pit

5BR Water View Home, Sauna, Game Room, Fire Pit
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (32 reviews)
"The property was amazing. The house was clean, beautiful, and well equipped. Plenty of space yet still cozy. Host was very communicative and gracious, had a pleasant experience and will definitely be back!"
United States
Maxx V.
The price is AED 1,612
AED 3,184 total
includes taxes & fees
15 Nov - 16 Nov
5BR Water View Home, Sauna, Game Room, Fire Pit

11. Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
Greenwich
10.0 out of 10, Exceptional, (2 reviews)
"Great location on the lake which the kids loved. The hosts were very friendly and easy to communicate with. The addition of the outdoor grill was a big plus and we enjoyed many afternoons out on the deck. We would stay again."
United States
Nathan R.
The price is AED 5,135
AED 8,160 total
includes taxes & fees
18 Nov - 19 Nov
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

12. 5BR Beach Home w/ Fireplaces, Fire Pit & Game Room

5BR Beach Home w/ Fireplaces, Fire Pit & Game Room
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (27 reviews)
"Very spacious and nicely decorated"
United States
Linda M.
The price is AED 1,723
AED 3,527 total
includes taxes & fees
15 Nov - 16 Nov
5BR Beach Home w/ Fireplaces, Fire Pit & Game Room

13. Coastal 5BR: Billiards, Ping Pong, Fire Pit, Yard

Coastal 5BR: Billiards, Ping Pong, Fire Pit, Yard
Cove - East Side - Shippan
9.6 out of 10, Exceptional, (27 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
United States
Maury A.
The price is AED 2,828
AED 4,869 total
includes taxes & fees
27 Nov - 28 Nov
Coastal 5BR: Billiards, Ping Pong, Fire Pit, Yard

14. Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
6.8 out of 10, (18 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is AED 579
AED 939 total
includes taxes & fees
18 Nov - 19 Nov
Centric property close to all the great things in the city

15. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is AED 691
AED 1,322 total
includes taxes & fees
18 Nov - 19 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

16. Private Single Fam, walk 2 train/ Theater- Dogs OK

Private Single Fam, walk 2 train/ Theater- Dogs OK
Greenwich
The price is AED 910
AED 2,873 total
includes taxes & fees
2 Dec - 3 Dec
Private Single Fam, walk 2 train/ Theater- Dogs OK

17. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (41 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is AED 734
AED 2,008 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

18. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
10.0 out of 10, Exceptional, (14 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is AED 533
AED 1,139 total
includes taxes & fees
7 Dec - 8 Dec
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

19. Elite room stay

Elite room stay
Bridgeport
The price is AED 760
AED 1,205 total
includes taxes & fees
15 Nov - 16 Nov
Elite room stay

20. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (43 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
The price is AED 826
AED 1,420 total
includes taxes & fees
16 Nov - 17 Nov
Contemporary Cozy Cottage
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.

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.

A stone dam with a waterfall, a bridge, and a forested hillside.

Top reviews in Pound Ridge