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

Holiday Homes in Pound Ridge

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Check prices for these dates

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

Our top choices for Pound Ridge holiday 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 AU$478
includes taxes & fees
5 Oct - 6 Oct
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 AU$561
includes taxes & fees
30 Sept - 1 Oct
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 AU$585
includes taxes & fees
13 Oct - 14 Oct
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 AU$373
includes taxes & fees
22 Sept - 23 Sept
Centric property close to all the great things in the city
Private kitchen

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 AU$1,081
includes taxes & fees
16 Sept - 17 Sept
Spacious Retreat with Game Room and Fire Pit
Private kitchen

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 AU$2,863
includes taxes & fees
19 Sept - 20 Sept
Private Country Getaway
Living area

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 AU$951
includes taxes & fees
16 Sept - 17 Sept
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Living area

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 AU$555
includes taxes & fees
23 Sept - 24 Sept
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Living area

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 AU$851
includes taxes & fees
14 Sept - 15 Sept
Spacious Stamford Home | Family, Work, Parking
Private kitchen

10. Elite room stay

Elite room stay
Bridgeport
The price is AU$477
includes taxes & fees
19 Sept - 20 Sept
Elite room stay
Private kitchen

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 AU$1,133
includes taxes & fees
15 Sept - 16 Sept
NYC-Area Escape Near River, Trails & MTA!
Living area

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 AU$997
includes taxes & fees
13 Sept - 14 Sept
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
Private kitchen

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 AU$1,015
includes taxes & fees
14 Sept - 15 Sept
Renovated Retreat with Heated Pool
Private kitchen

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 AU$846
includes taxes & fees
16 Sept - 17 Sept
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Beach

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 AU$887
includes taxes & fees
16 Sept - 17 Sept
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Living area

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.
The price is AU$1,579
includes taxes & fees
16 Sept - 17 Sept
5BR Beach House, Game Room + Huge Backyard
Private kitchen

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 AU$616
includes taxes & fees
5 Oct - 6 Oct
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 AU$760
includes taxes & fees
14 Sept - 15 Sept
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 AU$484
includes taxes & fees
5 Oct - 6 Oct
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Private kitchen

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 AU$799
includes taxes & fees
14 Sept - 15 Sept
"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.
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Top Pound Ridge Hotel Reviews

Hampton Inn & Suites Yonkers - Westchester

Hampton Inn & Suites Yonkers - Westchester

10/10 Excellent
"Clean rooms, great parking, kind staff."
Sank-yaw 1-night trip
Posted 5 hours ago
Hampton Inn & Suites Yonkers - Westchester

Find out more about Pound Ridge

Pound Ridge Holiday Homes information

Number of reviews
225
Accommodation
272 Holiday Homes
Lowest Price
AU$373
Highest Price
AU$2,863