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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Pound Ridge holiday homes

A campfire with a wooden table and benches by a 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, (43 reviews)
"Nice stay"
United States
Christopher J.
The price is NZ$557
includes taxes & fees
7 Oct - 8 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

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, (20 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is NZ$581
includes taxes & fees
6 Oct - 7 Oct
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

3. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is NZ$755
includes taxes & fees
4 Oct - 5 Oct
Gilded Age Luxury Surrounded by Nature
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

4. 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.
The price is NZ$1,257
includes taxes & fees
7 Oct - 8 Oct
5BR Beach Home | Walk to Cove Beach + Private Yard
A modern kitchen with white cabinets, a marble island, and black bar stools.

5. 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.
The price is NZ$1,410
includes taxes & fees
28 Oct - 29 Oct
Spacious Retreat with Game Room and Fire Pit
A modern living room with a white sofa, a glass coffee table, and a piano.

6. 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 NZ$1,154
includes taxes & fees
27 Oct - 28 Oct
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
A living room with a sofa set, a coffee table, and a television on a stand.

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 NZ$1,040
includes taxes & fees
4 Oct - 5 Oct
Spacious Stamford Home | Family, Work, Parking
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)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
The price is NZ$1,637
includes taxes & fees
14 Oct - 15 Oct
5BR Beach House, Water Views, Steps to Beach, Backyard
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

9. 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 NZ$1,236
includes taxes & fees
5 Oct - 6 Oct
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A modern bathroom with a black floor, a bench, a towel rack, and a mirror.

10. 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 NZ$1,682
includes taxes & fees
7 Oct - 8 Oct
5BR Beach House, Game Room + Huge Backyard
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

11. 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 NZ$1,261
includes taxes & fees
4 Oct - 5 Oct
Renovated Retreat with Heated Pool
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

12. 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 NZ$477
includes taxes & fees
6 Oct - 7 Oct
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.

13. 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, (1 review)
"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.
The price is NZ$3,741
includes taxes & fees
7 Oct - 8 Oct
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A two-story house with a brick facade and white trim, surrounded by lush greenery and trees.

14. 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.
The price is NZ$1,456
includes taxes & fees
21 Oct - 22 Oct
Snow Days & City Escapes: Spacious Ossining Home
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)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is NZ$662
includes taxes & fees
3 Nov - 4 Nov
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.

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, (41 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is NZ$1,055
includes taxes & fees
21 Oct - 22 Oct
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

17. Elite room stay

Elite room stay
Bridgeport
The price is NZ$604
includes taxes & fees
6 Oct - 7 Oct
Elite room stay
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

18. 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, (19 reviews)
"Place was very clean . Communication between owner and us was excellent."
United States
gail s.
The price is NZ$1,101
includes taxes & fees
7 Oct - 8 Oct
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

19. 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 NZ$756
includes taxes & fees
6 Oct - 7 Oct
Contemporary Cozy Cottage
A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

20. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is NZ$598
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
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

Hampton Inn & Suites Yonkers

8/10 Good
"NA"
Ross 1-night trip
Posted 14 hours ago
Hampton Inn & Suites Yonkers

Find out more about Pound Ridge

Pound Ridge Holiday Homes information

Number of reviews
327
Accommodation
263 Holiday Homes
Lowest Price
NZ$477
Highest Price
NZ$3,741