
Holiday rentals in Pound Ridge
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Top-rated holiday rentals in Pound Ridge
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Pound Ridge
Top guest favourite

Barn in Roxbury
5 out of 5 average rating, 44 reviewsFully Renovated Rural Barn
XenaRating, 5 stars3 weeks ago
My sister and I stayed at Kevin and Mina’s beautiful barn for 5 days. It was the perfect home base as we traveled through the neighboring towns on the Gilmore Girls trail. The house itself was specious, clean, well-decorated, and comfortable. It was great having the flexibility of enjoying the natural sunlight with the skylights open during the day and being able to sleep in a little with them closed overnight. Would definitely stay here again!
Top guest favourite

Home in Westport
5 out of 5 average rating, 55 reviewsWestport Deco HAUS /5 min to Town /10 min to Beach
AlexandraRating, 5 stars2 weeks ago
great location and loved the backyard
Guest favourite

Home in South Salem
4.95 out of 5 average rating, 43 reviewsHistoric Hideaway - Lake Access
LenoreRating, 5 stars2 weeks ago
Ever been on a historic home tour where part of the house is roped off & they say, "this is where the family used to live"? This felt like being allowed past the rope line and stepping into history. I can't imagine how much this costs to maintain & I'm happy to have helped with that. I can't imagine what it was like trying to update a home of this age to give it modern amenities, electricity, plumbing, and really cute bathrooms, but the host has done a great job. Taller than > 5'10", watch your head! Loved looking at the miniature fittings and furnishings and details of bygone days, the solid wood plank floors were particularly fascinating to me, tiny fireplace detailing, & some old rope and pulley windows with older glass are gorgeous. Very close to Le Chateau where we were attending a wedding. Extremely comfy beds & pillows. Great modernized bathrooms. Really unique spot.
Guest favourite

Home in Norwalk
5 out of 5 average rating, 68 reviewsNorwalk/Westport Border, Near Beach, w/Pizza Oven
DanaRating, 5 stars1 week ago
This home is well located. There is some street traffic, but once inside you don't really hear it. The kitchen had all the pots, pans, dishes, and glassware we needed. There was plenty of space for the 4 adults and 2 children . The outdoor deck was wonderful for a happy hour cool down after sight seeing and family visits. We all felt right at home. Thank you
Top guest favourite

Flat in Downtown Stamford
5 out of 5 average rating, 15 reviewsLuxurious 3BR/2BA Modern Haven Downtown Stamford
ChrisRating, 5 stars1 week ago
Wonderful stay! Beautiful apartment and great location. Extremely clean and comfortable place to stay. Loved our stay and would definitely return!
Top guest favourite

Guest house in Norwalk
5 out of 5 average rating, 21 reviewsWaterfront Getaway - Norwalk, CT
HillaryRating, 5 stars2 weeks ago
Loved our stay here! The apartment was very clean and comfortable, and had everything we needed. Excellent location - nice view and very walkable both to Sono and East Norwalk. Communication was easy and clear, thank you! Only thing I would note is that there is a flight of stairs to get to the entrance which was a little tricky with our luggage and stroller (we were traveling with a baby) - didn’t detract from how great our stay was, and would still book again despite that.
Guest favourite

Home in South Salem
4.92 out of 5 average rating, 12 reviews4 Seasons By The Lake 3 bedroom Luxurious Home
ChrissyRating, 5 stars2 months ago
Had a great stay at Lisa’s home! Perfect size for a small family. The streets were a little narrow so we didn’t quite feel comfortable walking the neighborhood, but the surroundings were beautiful and it was very quiet and seemed safe. Lisa’s home was stocked with anything we may have needed, and felt like home away from home. It’s off the beaten path a bit, but there are plenty of restaurants, stores, and places to explore just a short drive away. Lisa was protective and communicative throughout our stay.
Guest favourite

Home in Redding
5 out of 5 average rating, 36 reviewsQuiet and Cozy Cottage near NYC with a Pond
LouiseRating, 5 stars3 weeks ago
We loved Erin’s style, her beautiful cottage was comfortable and welcoming from the first. We found all we needed in the kitchen and everything worked well. The home was light and bright and well thought out. The grounds around the house were heavenly, with grassy dappled pathways through the woods and a gorgeous pond beyond the garden, with a river running through. Endless bird song and deer passing by, it was charming and peaceful. I highly recommend it.
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Jones Beach
- Fairfield Beach
- Yale University
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- Gilgo Beach
- United Nations Headquarters
- Statue of Liberty
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo