Pound Ridge, NY Vacation Homes from $266

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

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Our top choices for Pound Ridge vacation 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.

Greenwich

Christopher J.

$275 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

Waterside

Leslie S.

$286 nightly

Sep 30 - Oct 1

Total with taxes and fees

A bedroom with two beds, a nightstand with a lamp, a framed picture on the wall, and a window with curtains.

3. Gilded Age Luxury Surrounded by Nature

Cranbury

$377 nightly

Sep 28 - Sep 29

Total with taxes and fees

A modern kitchen with white cabinets, a marble island, and black bar stools.

4. Spacious Retreat with Game Room and Fire Pit

West Norwalk

Mark F.

$691 nightly

Sep 24 - Sep 25

Total with taxes and fees

A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

5. Centric property close to all the great things in the city

Brooklawn - St. Vincent

Alma B.

$235 nightly

Sep 23 - Sep 24

Total with taxes and fees

A living room with a sofa set, a coffee table, and a television on a stand.

6. Spacious Stamford Home | Family, Work, Parking

Cove - East Side - Shippan

james w.

$485 nightly

Sep 30 - Oct 1

Total with taxes and fees

A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

7. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Carmel Hamlet

Robert T.

$383 nightly

Sep 29 - Sep 30

Total with taxes and fees

8. 5BR Beach House, Game Room + Huge Backyard

Cove - East Side - Shippan

Kyra S.

$873 nightly

Sep 28 - Sep 29

Total with taxes and fees

A room with two beds, white curtains, a ceiling light, and a window with a view.

9. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

White Plains

"This guy is a scammer, an hour before my checkin they finally sent me the "location" and claimed they needed more time to clean the property. Then at 5 pm and hour after they claimed their was a gas leak and I couldn't stay there. Only thing is the address they sent me wasn't real and I am convinced this listing is fake in and used to trick people into staying at their actual property in yonkers. DO NOT RENT FROM THEM!"

Ethan G.

$474 nightly

Sep 23 - Sep 24

Total with taxes and fees

A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

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

White Plains

"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...

James D.

$480 nightly

Sep 23 - Sep 24

Total with taxes and fees

A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

11. Elite room stay

Bridgeport

$301 nightly

Sep 23 - Sep 24

Total with taxes and fees

A modern living room with a fireplace, a television, and a dining area with chairs and a table.

12. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Historic District

Melissa H.

$647 nightly

Oct 19 - Oct 20

Total with taxes and fees

A living room with two white sofas, a glass coffee table, a fireplace, and a flat-screen TV mounted above it.

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

West Side

Dave J.

$669 nightly

Oct 5 - Oct 6

Total with taxes and fees

A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

14. Contemporary Cozy Cottage

Lake Peekskill

Aj L.

$367 nightly

Sep 30 - Oct 1

Total with taxes and fees

A modern kitchen with a central island, pendant lights, and a view of the outdoors.

15. Renovated Retreat with Heated Pool

Redding

Alejandro A.

$673 nightly

Sep 27 - Sep 28

Total with taxes and fees

An outdoor patio with a fire pit, green chairs, and a table.

16. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

New Rochelle

Drew C.

$305 nightly

Oct 21 - Oct 22

Total with taxes and fees

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.

17. 5BR Beach House, Water Views, Game Room, Backyard

Cove - East Side - Shippan

Heather G.

$967 nightly

Oct 20 - Oct 21

Total with taxes and fees

A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

18. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Fairfield

Kim G.

$525 nightly

Oct 21 - Oct 22

Total with taxes and fees

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.

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

New Fairfield

Stephen L.

$310 nightly

Oct 18 - Oct 19

Total with taxes and fees

A room with a bed, a couch, a desk with a computer, and various wall decorations.

20. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Carmel Hamlet

$256 nightly

Sep 23 - Sep 24

Total with taxes and fees

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Top Pound Ridge Hotel Reviews

Hampton Inn White Plains/Tarrytown

10/10 Excellent

"L"

Sleepy Hollow Hotel, a Dolce by Wyndham

8/10 Good

"The hotel is nice, and clean, and they have the BEST big towels. But it doesn't have an actual restaurant or room service, which is very inconvenient. They also seem to have an issue around check-in. I was in a line of like 20 people, which was surprising. There was one desk clerk handling some sort of problem with one guest for 20 minutes. The other clerk moved glacially slow. Neither clerk seemed welcoming or customer service oriented. During this time, the manager came out several times to talk to the clerk handling the problem, but did not even look at or acknowlege the long line of people waiting. I would expect a manager to step in and help process the long line of check-ins. Another person came out several times and told people to use the check-in automatic kiosks, and several people said they had tried it already and it didn't even work. "Oh, sorry about that," she said. There's also a mystifying thing... the hallways and navigation are poorly marked, and it's not easy to figure out where you are going, or find an elevator. I was in a 3xx room, and when I got to the elevator, it said I was on floor 2 (which had the 4xx rooms). In the elevator, I had to press 1 to get to the floor with the 3xx rooms. ????? Didn't make sense! My recommendations: More check-in staff, better customer service training, and better signage for navigation."

Find out more about Pound Ridge

Pound Ridge Vacation Homes information

Number of reviews	249
Accommodation	280 Vacation Homes
Lowest Price	$266
Highest Price	$1,028

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Upfront pricing

Check prices for these dates

Our top choices for Pound Ridge vacation homes

1. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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

3. Gilded Age Luxury Surrounded by Nature

4. Spacious Retreat with Game Room and Fire Pit

5. Centric property close to all the great things in the city

6. Spacious Stamford Home | Family, Work, Parking

7. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

8. 5BR Beach House, Game Room + Huge Backyard

9. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups