Pound Ridge Vacation Rentals

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Check prices for these dates

Tonight
Dec 31 - Jan 1
Tomorrow
Jan 1 - Jan 2
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Pound Ridge vacation rentals

Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
2 bedrooms, iron/ironing board, travel crib, WiFi
Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is ￥16,508
￥45,344 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Renovated 2BR Retreat / Modern Comforts Included
2 bedrooms, in-room safe, desk, iron/ironing board
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is ￥17,528
￥42,705 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
Exclusive Apartment | Private kitchen | Mini-fridge, microwave, oven, stovetop
The Mansion Hotel-style

The Mansion Hotel-style

The Mansion Hotel-style
2.5 star property
West Norwalk
8.2 out of 10, Very Good, (22)
"Great service and very clean 👌 "
United States
JEAN
The price is ￥12,926
￥14,865 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Mansion Hotel-style
Fridge, microwave, oven, stovetop
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Brooklawn - St. Vincent
8.0 out of 10, Very Good, (1)
"It was clean "
United States
Burton
The price is ￥16,508
￥45,344 total
includes taxes & fees
Jan 9 - Jan 10, 2026
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.6 out of 10, Exceptional, (24)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
The price is ￥17,827
￥38,798 total
includes taxes & fees
Jan 1 - Jan 2, 2026
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Fridge, microwave, oven, stovetop
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (1)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
The price is ￥19,422
￥48,920 total
includes taxes & fees
Jan 28 - Jan 29, 2026
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Property grounds
Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (22)
"We stayed here for three nights, and it was very comfortable, clean and spacious. It's in a good location and the walk up to the second floor was not too bad. It was as advertised, and we would stay there again when in Bridgeport. "
United States
Robert C.
The price is ￥26,319
￥69,206 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Luxury Designer 2 bedroom+office/3bed vacation home.
Fridge, microwave, oven, stovetop
Bright Escape, Top-Rated Design, Fire pit, Near Beach

Bright Escape, Top-Rated Design, Fire pit, Near Beach

Bright Escape, Top-Rated Design, Fire pit, Near Beach
Fairfield
10.0 out of 10, Exceptional, (11)
"Great clean, kid-friendly house in just the location we wanted. Lots of thoughtful touches throughout the house that made our stay very comfortable. Would stay again!"
United States
Mary G.
The price is ￥27,763
￥74,919 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Bright Escape, Top-Rated Design, Fire pit, Near Beach
Lobby
Stamford Suites

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (84)
"Everything was good other than the two options for breakfast and housekeeping entering the hotel room unannounced or no knocking"
United States
Laila
The price is ￥17,219
￥19,802 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Stamford Suites
Standard Room, 1 King Bed, Main Building | Property entrance
Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (41)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is ￥42,757
￥49,170 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Guesthouse at Norwalk Inn
Exterior
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is ￥16,256
￥37,910 total
includes taxes & fees
Jan 4 - Jan 5, 2026
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Property grounds
Piermont Oasis

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (10)
"Easy check in; quick access to NYC. "
United States
Leah B.
The price is ￥18,716
￥32,831 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Piermont Oasis
1 bedroom, desk, iron/ironing board, free WiFi
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
10.0 out of 10, Exceptional, (3)
"Nice little spot with a great host."
United States
J M.
The price is ￥19,548
￥32,958 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Fridge, microwave, oven, stovetop
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (6)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is ￥20,744
￥47,452 total
includes taxes & fees
Jan 4 - Jan 5, 2026
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Fridge, microwave, oven, stovetop
Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is ￥21,111
￥57,039 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Modern Luxe 1BR Apt in Downtown Stamford
Fridge, microwave, oven, stovetop
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
10.0 out of 10, Exceptional, (2)
"Wonderful "
United States
Nolufefe Z.
The price is ￥24,425
￥59,595 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
Outdoor dining
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Fairfield
10.0 out of 10, Exceptional, (23)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is ￥27,763
￥75,014 total
includes taxes & fees
Jan 28 - Jan 29, 2026
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Outdoor dining
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (34)
"Stunning property!!"
United States
Samantha
The price is ￥38,603
￥68,258 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
2 bedrooms, iron/ironing board, WiFi, bed sheets
Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.

Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.

Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.
Downtown Bridgeport
9.0 out of 10, Wonderful, (2)
"Very convenient location to everything in Bridgeport. Very easy and explicit check in directions! The unit was very clean!"
United States
Kelly
The price is ￥38,993
￥60,361 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.
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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Top Pound Ridge Hotel Reviews

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

10/10 Excellent
"Very nice room and staff as usual "
Natalie 1-night trip
Posted 1 day ago
Norwalk Inn & Conference Center

Find out more about Pound Ridge

Search for holiday rentals in Pound Ridge on Expedia! You can easily find your home rentals, villas, holiday apartments in Pound Ridge using one of the methods below:

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Look no further and take a look at our great range of rental properties in Pound Ridge!

Frequently asked questions

Can I find a vacation rental in Pound Ridge?

Yes, there are vacation rentals close to well known points of interest in Pound Ridge, or you can choose a more remote option if you're looking for relaxation. Pound Ridge is known for its sporting events and museums.

What are some of the best vacation home rentals that Pound Ridge has to offer?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: Visitors like this Pound Ridge vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Pound Ridge?

With 7 Expedia vacation rentals, you're sure to find just the right place for your Pound Ridge stay.

What can I see and do in Pound Ridge?

Pound Ridge Town Park and Mianus River Gorge Preserve are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Caramoor Center for Music and the Arts and The Glass House.

What are vacation rentals like in Pound Ridge?

Vacation rentals are privately owned properties you can book for a couple days or more in Pound Ridge. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.