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

Pound Ridge Vacation Rentals

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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)
"This is a beautiful property. Great location. And the hosts are very nice and very great in communicating everything. Loved staying there"
United States
Martina F.
The price is CA $325
CA $559 total
includes taxes & fees
Sep 22 - Sep 23
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, (18 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is CA $270
CA $518 total
includes taxes & fees
Sep 15 - Sep 16
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Room

3. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is CA $324
CA $595 total
includes taxes & fees
Sep 28 - Sep 29
Gilded Age Luxury Surrounded by Nature
Living area

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 CA $218
CA $372 total
includes taxes & fees
Sep 11 - Sep 12
Centric property close to all the great things in the city
Private kitchen

5. 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 CA $1,799
CA $2,840 total
includes taxes & fees
Sep 13 - Sep 14
Private Country Getaway
Private kitchen

6. 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 CA $412
CA $980 total
includes taxes & fees
Sep 10 - Sep 11
Spacious Retreat with Game Room and Fire Pit
Living area

7. 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 CA $383
CA $783 total
includes taxes & fees
Sep 8 - Sep 9
Spacious Stamford Home | Family, Work, Parking
Living area

8. 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.
The price is CA $563
CA $1,291 total
includes taxes & fees
Sep 8 - Sep 9
5BR Beach House, Game Room + Huge Backyard
Private kitchen

9. Elite room stay

Elite room stay
Bridgeport
The price is CA $286
CA $475 total
includes taxes & fees
Sep 8 - Sep 9
Elite room stay
Living area

10. 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 CA $410
CA $977 total
includes taxes & fees
Sep 9 - Sep 10
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Outdoor dining

11. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
The price is CA $374
CA $782 total
includes taxes & fees
Sep 15 - Sep 16
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Interior

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 CA $509
CA $963 total
includes taxes & fees
Sep 9 - Sep 10
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
Living area

13. 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 CA $324
CA $601 total
includes taxes & fees
Sep 21 - Sep 22
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Living area

14. 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 CA $374
CA $757 total
includes taxes & fees
Sep 8 - Sep 9
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
Interior

15. 5BR Beach House, Water Views, Game Room, Backyard

5BR Beach House, Water Views, Game Room, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
The price is CA $657
CA $1,325 total
includes taxes & fees
Sep 22 - Sep 23
5BR Beach House, Water Views, Game Room, Backyard
Beach

16. 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 CA $293
CA $804 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Private kitchen

17. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is CA $535
CA $1,150 total
includes taxes & fees
Sep 27 - Sep 28
Renovated Retreat with Heated Pool
Private kitchen

18. 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 CA $346
CA $622 total
includes taxes & fees
Sep 30 - Oct 1
Contemporary Cozy Cottage
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, (9 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is CA $203
CA $481 total
includes taxes & fees
Oct 5 - Oct 6
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
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

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Pound Ridge Vacation Homes information

Number of reviews
Accommodation
276 Vacation Homes
Lowest Price
CA $1,707
Highest Price
CA $2,073

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