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

Search Vacation Homes in Pound Ridge

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (45 reviews)
"Nice stay"
United States
Christopher J.
$349 nightly
The price is $395
Oct 25 - Oct 26
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A residential backyard with a lawn, a shed, and a house.

2. 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, (21 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
$411 nightly
The price is $466
Oct 25 - Oct 26
Total with taxes and fees
Gem by the water+ firepit and all fenced backyard
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
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay."
United States
Linda S.
$666 nightly
The price is $755
Nov 18 - Nov 19
Total with taxes and fees
Spacious Retreat with Game Room and Fire Pit
A living room with a sofa set, a coffee table, and a television on a stand.

4. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
$461 nightly
The price is $522
Oct 26 - Oct 27
Total with taxes and fees
Spacious Stamford Home | Family, Work, Parking
A modern living room with a white sofa, a glass coffee table, and a piano.

5. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
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.
$561 nightly
The price is $635
Oct 27 - Oct 28
Total with taxes and fees
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
A bedroom with a wooden staircase, two beds, a nightstand, and a wall-mounted lamp.

6. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
$495 nightly
The price is $564
Oct 21 - Oct 22
Total with taxes and fees
Gilded Age Luxury Surrounded by Nature
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

7. 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, (15 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.
$587 nightly
The price is $665
Nov 9 - Nov 10
Total with taxes and fees
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
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.

8. 5BR Beach House, Water Views, Steps to Beach, Backyard

5BR Beach House, Water Views, Steps to Beach, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 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.
$926 nightly
The price is $983
Nov 1 - Nov 2
Total with taxes and fees
5BR Beach House, Water Views, Steps to Beach, Backyard
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.
$605 nightly
The price is $685
Oct 22 - Oct 23
Total with taxes and fees
Renovated Retreat with Heated Pool
A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

10. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
Ossining
8.2 out of 10, Very good, (19 reviews)
"A family trip with teens and tweens- a perfect space! Clean, hist was friendly, the house was stocked with all we'd need! A great getaway for any family NYC trip!"
United States
Justeen P.
$682 nightly
The price is $760
Oct 21 - Oct 22
Total with taxes and fees
Snow Days & City Escapes: Spacious Ossining Home
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

11. 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.
$205 nightly
The price is $233
Oct 21 - Oct 22
Total with taxes and fees
Centric property close to all the great things in the city
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

12. 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.
$2,170 nightly
The price is $2,455
Nov 1 - Nov 2
Total with taxes and fees
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

13. 5BR Beach Home | Walk to Cove Beach + Private Yard

5BR Beach Home | Walk to Cove Beach + Private Yard
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 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.
$628 nightly
The price is $667
Oct 27 - Oct 28
Total with taxes and fees
5BR Beach Home | Walk to Cove Beach + Private Yard
Open concept kitchen

14. 5BR Beach House, Game Room + Huge Backyard

5BR Beach House, Game Room + Huge Backyard
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (26 reviews)
"Very spacious and nicely decorated"
United States
Linda M.
$832 nightly
The price is $883
Oct 27 - Oct 28
Total with taxes and fees
5BR Beach House, Game Room + Huge Backyard
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

15. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (41 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
$367 nightly
The price is $420
Oct 21 - Oct 22
Total with taxes and fees
Contemporary Cozy Cottage
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

16. 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.
$324 nightly
The price is $351
Nov 3 - Nov 4
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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.
$487 nightly
The price is $551
Oct 21 - Oct 22
Total with taxes and fees
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

18. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
$868 nightly
The price is $892
Nov 3 - Nov 4
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

19. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
$1,001 nightly
The price is $1,115
Nov 3 - Nov 4
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

20. Elite room stay

Elite room stay
Bridgeport
$301 nightly
The price is $341
Oct 21 - Oct 22
Total with taxes and fees
Elite room stay
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

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"Property has everything you could want including a movie theater! Beautiful hotel!"
Linda 2-night trip
Posted 4 hours ago
Hyatt Regency Greenwich

Find out more about Pound Ridge

Pound Ridge Vacation Homes information

Number of reviews
314
Accommodation
266 Vacation Homes
Lowest Price
$233
Highest Price
$2,455

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