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

Search Vacation Homes in Pound Ridge

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Pound Ridge vacation homes

Property grounds

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, (42 reviews)
"Nice stay"
United States
Christopher J.
The price is ￥29,186
￥53,380 total
includes taxes & fees
Oct 4 - Oct 5
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Property grounds

2. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is ￥29,585
￥57,832 total
includes taxes & fees
Sep 15 - Sep 16
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
2 bedrooms, iron/ironing board, WiFi, bed sheets

3. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is ￥35,945
￥65,607 total
includes taxes & fees
Sep 28 - Sep 29
Gilded Age Luxury Surrounded by Nature
Smart TV

4. 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
6.6 out of 10, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is ￥24,194
￥40,804 total
includes taxes & fees
Sep 14 - Sep 15
Centric property close to all the great things in the city
Coffee/tea maker, fridge, microwave, oven

5. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
10.0 out of 10, Exceptional, (2 reviews)
"A great location. We were less than 15 minutes from everything we did. House was a super layout for our large group."
United States
Mark F.
The price is ￥53,088
￥116,103 total
includes taxes & fees
Sep 16 - Sep 17
Spacious Retreat with Game Room and Fire Pit
Coffee/tea maker, fridge, microwave, oven

6. Private Country Getaway

Private Country Getaway
Bedford Hills
9.6 out of 10, Exceptional, (4 reviews)
"We had a busy and lovely weekend to attend and be part of my nieces wedding. The location was perfect and the property is beautiful. Kitchen was perfect for gathering in the morning and the great room was big and comfy for catching up! "
United States
Karin R.
The price is ￥199,693
￥322,321 total
includes taxes & fees
Sep 20 - Sep 21
Private Country Getaway
Smart TV, fireplace, books, stereo

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.
The price is ￥45,760
￥107,370 total
includes taxes & fees
Sep 16 - Sep 17
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
TV, fireplace

8. 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
9.8 out of 10, Exceptional, (20 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥31,797
￥61,430 total
includes taxes & fees
Sep 23 - Sep 24
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
TV

9. 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.
The price is ￥46,851
￥91,974 total
includes taxes & fees
Sep 15 - Sep 16
Spacious Stamford Home | Family, Work, Parking
Private kitchen

10. Elite room stay

Elite room stay
Bridgeport
The price is ￥31,797
￥52,388 total
includes taxes & fees
Sep 14 - Sep 15
Elite room stay
Coffee/tea maker, fridge, microwave, stovetop

11. NYC-Area Escape Near River, Trails & MTA!

NYC-Area Escape Near River, Trails & MTA!
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.
The price is ￥33,641
￥126,260 total
includes taxes & fees
Sep 15 - Sep 16
NYC-Area Escape Near River, Trails & MTA!
TV

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

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.4 out of 10, Exceptional, (8 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 ￥66,206
￥118,149 total
includes taxes & fees
Sep 14 - Sep 15
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
Coffee/tea maker, fridge, microwave, oven

13. 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 ￥46,175
￥109,819 total
includes taxes & fees
Sep 15 - Sep 16
Renovated Retreat with Heated Pool
Coffee/tea maker, fridge, microwave, oven

14. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (18 reviews)
"Place was very clean . Communication between owner and us was excellent."
United States
gail s.
The price is ￥34,977
￥88,873 total
includes taxes & fees
Sep 16 - Sep 17
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Beach nearby, sun loungers, beach towels

15. 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, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is ￥39,171
￥97,382 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Smart TV, fireplace, foosball, table tennis

16. 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)
"Great stay!"
United States
Kyra S.
5BR Beach House, Game Room + Huge Backyard
Coffee/tea maker, fridge, microwave, oven

17. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (40 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is ￥38,403
￥67,114 total
includes taxes & fees
Sep 30 - Oct 1
Contemporary Cozy Cottage
Living area

18. Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC

Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
White Plains
2.0 out of 10, (1 review)
"An hour before check-in we were called by the property manager, after four days of messaging them through the app without response, to advise us that the property had an alleged water pipe burst and was unavailable, then attempted to upcharge us for alternate accommodations. An alternate place to stay was finally provided at no additional charge but much smaller than what had been booked. Given the absence of communication for four days and then a sudden incident the day of check-in - the day...
United States
James D.
The price is ￥41,475
￥84,334 total
includes taxes & fees
Sep 14 - Sep 15
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
Terrace/patio

19. 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
9.8 out of 10, Exceptional, (10 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is ￥23,042
￥54,468 total
includes taxes & fees
Oct 5 - Oct 6
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Coffee/tea maker, fridge, microwave, oven

20. "Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is ￥30,415
￥88,450 total
includes taxes & fees
Sep 14 - Sep 15
"Country outside the city " 3 bedrooms 2 full bathrooms
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

Westchester Marriott

Westchester Marriott

10/10 Excellent
"Wonderful place, enjoyed the lobby and restaurant on premises. Will definitely recommend."
Herminia 1-night trip
Posted 3 hours ago
Westchester Marriott

Find out more about Pound Ridge

Pound Ridge Vacation Homes information

Number of reviews
225
Accommodation
272 Vacation Homes
Lowest Price
￥40,804
Highest Price
￥322,321