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Compare 402 Vacation Homes in Pound Ridge with updated reviews, rates, and availability.

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (9)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (20)
"This property was perfect for our weekend trip to celebrate my nieces family/birthday weekend at Fairfield"
Lakeside luxury: beautiful, relaxing 4 bedroom home

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

10.0 out of 10, Exceptional, (105)
"My friends and I were in town for a wedding."
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

8.8 out of 10, Excellent, (30)
"Its was perfect, quiet and spacious great little get away."
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (30)
"Great communication and accommodations from the host. We were in town for a concert and the location couldn't have been better! Would recommend this stay for anyone looking within the area."
Cheerful 4 bedrooms residential house.

Modern 4BD/3BA w/Parking & deck & 29 min>NYC

9.6 out of 10, Exceptional, (11)
"Location was great! Having a car with off street parking, walk to station and well lit. Very clean, hot hot water (which I loved!) and plenty in the kitchen! Thank you!"
Modern 4BD/3BA w/Parking & deck & 29 min>NYC

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (28)
"We stayed for 3 weeks it was lovely!"
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"Very convenient and plenty of room. Easy to get to NY from Stamford train station and everything we needed nearby."
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (18)
"Our stay was lovely. Nadia was a wonderful host and the property was so welcoming."
The price is AEDĀ 918
AEDĀ 1,587 total
includes taxes & fees
12 May - 13 May
Contemporary Cozy Cottage

Modern, Magical Woodsy Escape 1 Hour From NYC

10.0 out of 10, Exceptional, (24)
"great place beautiful setting. The house looks nicer than what is actually in the listing. Comfortable place, very clean, had everything we needed. "
Modern, Magical Woodsy Escape 1 Hour From NYC

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"We were a family of 4 adults and 2 toddlers staying over Thanksgiving. We really didn’t need all the space but we certainly enjoyed it. There’s a huge well stocked kitchen, kids’ play areas on both the main floor and basement, and the property is massive and gorgeous. Great stay!"
Over Sized Colonial on Private Road.

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (20)
"We had a great time and it was a very spacious and clean location "
The price is AEDĀ 2,160
AEDĀ 3,956 total
includes taxes & fees
20 May - 21 May
New Beach Home near Stamford Downtown/Shippan

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

9.6 out of 10, Exceptional, (11)
"My family and I stayed here for a few days while skiing at Thunder Ridge. Would definitely come back in the spring or summer to enjoy kayaking on the pond and hiking along local trails. Highly recommend this cottage. "
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Charming 2-bedroom house with AC, WiFi in marvelous Nyack

2.0 star property
10.0 out of 10, Exceptional, (1)
"I have stayed in several vacation homes in Nyack. Some were swankier, most were cleaner or better stocked, but none was more comfortable or in a better location. The neigborhood is quiet, the house has loads of privacy, and you can easily walk to anything in town. There is a short but very steep part on this walk, so bring some sneakers if walking in town is your thing. This is the perfect place to stay if you want to feel as though you LIVE in Nyack. This was my fourth stay at this house. "
Charming 2-bedroom house with AC, WiFi in marvelous Nyack

Cottage at Sunny Day- Lakeside, views, kayak, dock

9.8 out of 10, Exceptional, (36)
"Great place magnificent views. It’s a very peaceful place"
Cottage at Sunny Day- Lakeside, views, kayak, dock

Westport Gem - walk to shops, dining, town center, pet-friendly

10.0 out of 10, Exceptional, (3)
"Had a great time! My favorite part was sitting on the back deck w coffee in the morning. There were so many birds and the tall hedges that protected the privacy was so charming. The host was so nice and left out fruit and snacks. Loved staying there!"
Westport Gem - walk to shops, dining, town center, pet-friendly

Charming Mamaroneck Home ~ 22 Mi to Manhattan

7.8 out of 10, Good, (12)
"Clean and easy check in--Great Location!"
Charming Mamaroneck Home ~ 22 Mi to Manhattan

NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

10.0 out of 10, Exceptional, (5)
"We had a wonderful vacation with our grandchildren and family. The children lived in the water if not kayaking or water boards they were fishing!! Rainy days puzzles were our entertainment the summer house provided everything one wanted or needed. It was a very delightful vacation"
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

Ossining Vacation Rental Near River, Trails & MTA!

7.6 out of 10, Good, (8)
"This was our Christmas gathering place for family from 4 states. Beautiful home and location. "
Ossining Vacation Rental Near River, Trails & MTA!
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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Other property types in Pound Ridge

Stamford Suites

3.0 star property
6.0 out of 10, (29)
"Convenience. Full kitchen and spacious rooms"
The price is AEDĀ 644
AEDĀ 740 total
includes taxes & fees
14 May - 15 May
Stamford Suites

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (53)
"Absolutely perfect location for visiting Fairfield University! Everything about it exceeded our expectations."
The price is AEDĀ 793
AEDĀ 1,114 total
includes taxes & fees
12 May - 13 May
DUNE Fairfield Beach

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (16)
"Vibe and aesthetic was lovely - near downtown restaurants, wonderful time will come back "
Luxury Apartments by Hyatus at The Asher
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.