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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

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

Historic Connecticut Home w/ Grill & Spacious Yard
Dining

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (6)
"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
Property grounds

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (19)
"This is a beautiful property. When we arrived, everything was perfect. It is completely stocked, including games for the family, and an unbelievable view of the lake. Communication with the homeowner was wonderful and we definitely plan to come back. We highly recommend this beautiful, clean and well kept home on the lake!."
Lakeside luxury: beautiful, relaxing 4 bedroom home
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
Outdoor spa tub

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

10.0 out of 10, Exceptional, (106)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Fridge, microwave, oven, stovetop

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (27)
"Perfect place and plenty of parking. "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Cheerful 4 bedrooms residential house.
Fridge, microwave, dishwasher, coffee/tea maker

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (30)
"Toocold in Connecticut, host was alway inclose contact, heat was our only issue "
Cheerful 4 bedrooms residential house.
Modern 4BD/3BA w/Parking & deck & 29 min>NYC
Point of interest

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

9.6 out of 10, Exceptional, (10)
"House was very nice and roomy. Area was nice also. Had an issue upstairs with refrigerator but used downstairs one as a backup."
Modern 4BD/3BA w/Parking & deck & 29 min>NYC
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Outdoor dining

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

9.8 out of 10, Exceptional, (28)
"Our family's stay at Helen and Richie's property for the holidays was perfect. Waking up to views of the lake every morning, watching flocks of birds travel on the water and being surrounded by nature was all we could ask for. The house has all amenities provided in the kitchen, bathrooms etc. Location is convenient near shops, grocery, and restaurants in New Fairfield. The hosts were very responsive in communication and I appreciated them providing everything we needed. "
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Fridge, microwave, oven, stovetop

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"House is absolutely perfect! This is our second time staying and we will definitely return. So much charm and warmth. I had the best sleep that I have had in months. All the amenities you could ask for, and more. Terrific convenient location. Host goes above and beyond to make sure we are comfortable. "
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Main Street Westport, walk to shops, dining, downtown
Miscellaneous

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown
Contemporary Cozy Cottage
Interior

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (17)
"This is a fully decked out house with cozy beds, full kitchen, completely up to date amenities. The host is very accessible, polite, and helpful."
The price is AED 918
AED 1,526 total
includes taxes & fees
9 Apr - 10 Apr
Contemporary Cozy Cottage
Modern, Magical Woodsy Escape 1 Hour From NYC
Fridge, microwave, oven, stovetop

Modern, Magical Woodsy Escape 1 Hour From NYC

10.0 out of 10, Exceptional, (22)
"The home was beautiful, comfortable and so spacious. Great time with friends made even better by the location. The amenities were great, beds were so comfortable and quality toiletries provided. Would definitely considering coming back. Not one complaint. Host set us up to have a winderful weekend. "
Modern, Magical Woodsy Escape 1 Hour From NYC
Over Sized Colonial on Private Road.
Exterior

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"The home was spacious and provided recreation for kids with hot tub, gym, ping pong, foosball, and game. However, property was advertised as 9 bedrooms and 7 baths. My family looked forward to spreading out but 4 bedrooms with adjoining bathrooms were locked. Text host to see if he would open them but he declined. That was disappointing."
Over Sized Colonial on Private Road.
New Beach Home near Stamford Downtown/Shippan
Terrace/patio

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (20)
"Great home with fun ping pong table!"
The price is AED 1,870
AED 3,558 total
includes taxes & fees
13 Apr - 14 Apr
New Beach Home near Stamford Downtown/Shippan
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Outdoor dining

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

9.6 out of 10, Exceptional, (11)
"I was pleasantly surprised! The house looked even better in person than it did in the photos. It is warm and comfortable and they had everything we needed to enjoy our time away. The house was clean and the surrounding property was well maintained. I would love to come back in the spring/summer to enjoy more of the outdoors. "
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
Private kitchen

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

2.0 star property
Charming 2-bedroom house with AC, WiFi in marvelous Nyack
Cottage at Sunny Day- Lakeside, views, kayak, dock
Miscellaneous

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

9.8 out of 10, Exceptional, (35)
"This property was very new and clean. It had everything you needed. Every room was comfortable and had its own TV. The open layout of the main floor made for great socializing and eating, and the 180 views of the frozen lake (in February) were beautifully serene. Would definitely come again and maybe next time in the summer! Thanks you for sharing this lovely property."
Cottage at Sunny Day- Lakeside, views, kayak, dock
Westport Gem - walk to shops, dining, town center, pet-friendly
Miscellaneous

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

10.0 out of 10, Exceptional, (3)
"After a rough year we were able to get a few days away and at the last minute chose this location. Everything we were looking for was there. The home and grounds were beautiful. The location in Westport was exactly what we wanted: magnificent fall foliage, quiet where the home was but close enough to walk to town and enjoy every aspect of being close by the town for lovely cafes and restaurants. Also, beautiful places were accessible by car in minutes such as Earthplace for trails and nature...
Westport Gem - walk to shops, dining, town center, pet-friendly
Charming Mamaroneck Home ~ 22 Mi to Manhattan
TV

Charming Mamaroneck Home ~ 22 Mi to Manhattan

7.8 out of 10, Good, (11)
"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!
Smart TV

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

10.0 out of 10, Exceptional, (5)
"This place is amazing!! The house had everything we needed and more. We really enjoyed our stay and also be able to host some of our family in the area was precious. My daughters rented equipment for the babies which worked out well. The house is very spacious and 5 adults and 3 children fit nicely. Very highly recommend. The pier was fun to hang out on but due to weather we were to enjoy the lake as much. Easy to find, and owners were very responsive. "
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!
Ossining Vacation Rental Near River, Trails & MTA!
Fridge, microwave, stovetop, dishwasher

Ossining Vacation Rental Near River, Trails & MTA!

8.4 out of 10, Very Good, (7)
"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

Over Sized Colonial on Private Road.
Exterior

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"The home was spacious and provided recreation for kids with hot tub, gym, ping pong, foosball, and game. However, property was advertised as 9 bedrooms and 7 baths. My family looked forward to spreading out but 4 bedrooms with adjoining bathrooms were locked. Text host to see if he would open them but he declined. That was disappointing."
Over Sized Colonial on Private Road.
DUNE Fairfield Beach
Private beach nearby, sun loungers, beach umbrellas, beach towels

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (50)
"Really liked Dune. I had a great room that was on the other side from Sea Grape - bar that could be loud. I heard noting from room 31. Could walk to Post Rd and the beach. Ocean view from room. "
The price is AED 834
AED 1,162 total
includes taxes & fees
14 Apr - 15 Apr
DUNE Fairfield Beach
Stamford Suites
Exterior

Stamford Suites

3.0 star property
5.6 out of 10, (24)
"Room was very spacious "
The price is AED 636
AED 732 total
includes taxes & fees
24 Apr - 25 Apr
Stamford Suites
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.