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

Search Vacation Homes in Pound Ridge

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Pound Ridge vacation homes

A dock with kayaks and a canoe, surrounded by trees and a calm lake.

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.
$293 nightly
The price is $333
Nov 18 - Nov 19
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A two-story house with a front porch, a chimney, and a well-maintained garden with a stone pathway leading to the entrance.

2. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
$357 nightly
The price is $408
Nov 18 - Nov 19
Total with taxes and fees
Gilded Age Luxury Surrounded by Nature
A modern kitchen with white cabinets, a marble island, and black bar stools.

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.
$666 nightly
The price is $758
Nov 18 - Nov 19
Total with taxes and fees
Spacious Retreat with Game Room and Fire Pit
An outdoor seating area with a round table, a chair, and a hanging light fixture.

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.
$390 nightly
The price is $445
Nov 17 - Nov 18
Total with taxes and fees
Gem by the water+ firepit and all fenced backyard
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a built-in oven.

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.
$514 nightly
The price is $585
Nov 19 - Nov 20
Total with taxes and fees
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ
A modern living room with a white sofa, a glass coffee table, and a piano.

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.
$487 nightly
The price is $555
Nov 16 - Nov 17
Total with taxes and fees
Spacious 3BR Townhome | Garage + Near Downtown
A living room with a sofa, armchair, ottoman, and coffee table.

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.
$423 nightly
The price is $482
Nov 16 - Nov 17
Total with taxes and fees
Spacious 3BR | Family + Work | Ample Parking
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

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.
$531 nightly
The price is $605
Nov 17 - Nov 18
Total with taxes and fees
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

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.
$577 nightly
The price is $658
Nov 16 - Nov 17
Total with taxes and fees
Renovated Retreat with Heated Pool
A modern kitchen with granite countertops, a dining area with black chairs, a living room with a sofa and a coffee table, and a large window with a view.

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.
$990 nightly
The price is $1,051
Dec 2 - Dec 3
Total with taxes and fees
5BR Water View Home, Sauna, Game Room, Fire Pit
A living room with a green sofa, a wooden desk with a computer, a lamp, and a sign that reads "LAKE HOUSE".

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.
$1,952 nightly
The price is $2,222
Nov 18 - Nov 19
Total with taxes and fees
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
Open concept kitchen

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.
$936 nightly
The price is $994
Nov 18 - Nov 19
Total with taxes and fees
5BR Beach Home w/ Fireplaces, Fire Pit & Game Room
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

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.
$913 nightly
The price is $970
Nov 16 - Nov 17
Total with taxes and fees
Coastal 5BR: Billiards, Ping Pong, Fire Pit, Yard
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

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.
$225 nightly
The price is $256
Nov 18 - Nov 19
Total with taxes and fees
Centric property close to all the great things in the city
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

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)
"Great place"
United States
Christopher P.
$332 nightly
The price is $360
Nov 18 - Nov 19
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A patio with a wooden fence, a table with chairs, and raised planters.

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

Private Single Fam, walk 2 train/ Theater- Dogs OK
Greenwich
$780 nightly
The price is $787
Dec 9 - Dec 10
Total with taxes and fees
Private Single Fam, walk 2 train/ Theater- Dogs OK
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

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.
$482 nightly
The price is $549
Nov 17 - Nov 18
Total with taxes and fees
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
An outdoor patio with a fire pit, green chairs, and a table.

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.
$253 nightly
The price is $289
Nov 16 - Nov 17
Total with taxes and fees
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

19. Elite room stay

Elite room stay
Bridgeport
$289 nightly
The price is $329
Nov 16 - Nov 17
Total with taxes and fees
Elite room stay
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

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.
$338 nightly
The price is $387
Nov 16 - Nov 17
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pound Ridge Hotel Reviews

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

10/10 Excellent
"Beautiful and close to great restaurants and shopping, friendly style comfortable room"
Tawni 1-night trip
Posted 14 hours ago
Norwalk Inn & Conference Center

Find out more about Pound Ridge

Pound Ridge Vacation Homes information

Number of reviews
195
Accommodation
266 Vacation Homes
Lowest Price
$256
Highest Price
$2,222

Explore a world of travel with Expedia