Holiday Homes in Pound Ridge

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Featured Holiday Homes in Pound Ridge

Escape to a Celebrity Chef's Waterfront Lake House

10.0 out of 10, Exceptional, (1)
Escape to a Celebrity Chef's Waterfront Lake House

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

10.0 out of 10, Exceptional, (16)
"My time spent at the lake house with my family was unforgettable. Nestled along the serene shoreline, the house offered stunning lake views from every window. Mornings began with coffee on the spacious deck, watching the sun rise over the water. Days were filled with family fun. The house itself was cozy yet modern, with plush furnishings, a crackling fireplace, and a fully-equipped kitchen where we cooked meals together. Evenings were spent playing board games, hanging out by the fire pit. It...
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (94)
"Dierdre's home was a perfect spot for our family Thanksgiving. Well located, well stocked, and very well cared for!"
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Historic Hideaway with Lake Access!

9.6 out of 10, Exceptional, (14)
"We were in town for work for the week and found this site online. Great spot, nice a quiet. "
Historic Hideaway with Lake Access!

'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

10.0 out of 10, Exceptional, (24)
"Would stay here again "
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

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

2.0 star property
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

8.8 out of 10, Excellent, (25)
"Akuvi is an outstanding host. Prior to and during our stay he was immediately responsive to all of the messages/requests I sent him. The listing on VRBO is accurate and if you look at the description and pictures you'll get exactly what you're looking at"
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (18)
"We had a friend group boardgaming weekend and this was perfect for our purposes. The table was large enough for our biggest games and the pool table doubled as a backup playing space. The race cars are a nice touch of whimsy too :-) Our only suggestion would be to replace the oversized, too-low chandelier over the table but really only a minor thing."
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (25)
"Great place, great service!!"
Lakeview Estate - Chef's Kitchen - NYC Getaway

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

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (18)
"This was a late holiday gathering of family members from St. Louis and Rye New York. Great and easy spot to get to. Pretty setting with the water view. I am sure in warmer seasons it be great spot for all the outside amenities. Six adults and one baby. Space nice set up. "
Waterview House Walking Distance from Cove Beach

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (26)
"The house was clean, comfortable, and kitchen was great. Only problem was stairs for my handicapped sister-too steep but possible. Manager very nice"
Cheerful 4 bedrooms residential house.

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (18)
"We were 9 adult women. There was plenty of space for us to gather as a group as well as sleep. The house is clean and in a great neighborhood. Very easy on and off to the highway to get to our conference in Darien. Highly recommend."
The price is AU$1,200
includes taxes & fees
24 Feb - 25 Feb
New Beach Home near Stamford Downtown/Shippan

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (13)
"Beautiful modern home with great views over the pond and woods. Super comfortable and many amenities. I really appreciated how well stocked the kitchen was with pots and pans that you can actually cook with compared to most VRBO's. Only drawback is that the area isn't really walkable. Busy road with minimal shoulder and you can't get down to the pond. We drove to a number of great hikes in the area though. Bonus: the woods behind the house were home to a couple great horned owls calling to...
The price is AU$1,459
includes taxes & fees
26 Feb - 27 Feb
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (15)
"We had a wonderful stay at the Contemporary Cozy Cottage! Very modern amenities and appliances, and the kitchen had everything we needed!! Nadia always responded promptly, and answered all of my questions. The Cottage is located close to just about everything in the Peekskill, Cortlandt Manor, and Yorktown Heights area. And I would definitely recommend a short drive to the charming little town of Cold Spring which is not too far away. Thank you Nadia!"
The price is AU$599
includes taxes & fees
17 Mar - 18 Mar
Contemporary Cozy Cottage

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (18)
"We enjoyed the lovely view of the lake and our wonderful, brisk walks in the neighborhood. The spacious and well-appointed lake home was perfect of our family with young adult children. We loved this beautiful, comfortable and entertaining home on the lake and hope to return."
Lakeside luxury: beautiful, relaxing 4 bedroom home

Seaview Ave House-4BR/8PPL Retreat

9.8 out of 10, Exceptional, (8)
"This was an awesome place to stay. Very clean and well kept. When I needed to get in touch for some last minute questions, the owner was very prompt and eager to help. I would definitely stay here again."
The price is AU$1,010
includes taxes & fees
23 Feb - 24 Feb
Seaview Ave House-4BR/8PPL Retreat

Lakefront Cottage with Private Dock, Kayaks, Stunning Lake Views, Modern Renovations and Family Fun

9.8 out of 10, Exceptional, (33)
"I spent a week at the Cottage at Sunny Day in mid January and it was just what I was looking for. I wanted a quiet, relaxing retreat in a beautiful location. The house was immaculate and very comfortable. Everything was provided, and there was a great fireplace and a beautiful view of Lake Taunton. Jenna and Tony were very nice and easy to deal with and made sure that everything was perfect. It would be a great stay at any time, but would be especially nice in the warm weather with direct access...
Lakefront Cottage with Private Dock, Kayaks, Stunning Lake Views, Modern Renovations and Family Fun
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.

9.6 out of 10, Exceptional, (38)
"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.

Global Luxury Suites White Plains

3.5 star property
7.0 out of 10, Good, (28)
"Great location, friendly people, great apartment "
Global Luxury Suites White Plains

Stamford Suites

3.0 star property
5.6 out of 10, (23)
"Room was very spacious "
The price is AU$306
includes taxes & fees
8 Mar - 9 Mar
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.