A serene park with a pond, a small boat, and autumn-colored trees.

Pound Ridge Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Pound Ridge vacation rentals

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (161 reviews)
"The front desk gentleman that checked us in was excellent!!"
United States
Selena
The price is CA $179
CA $206 total
includes taxes & fees
Aug 19 - Aug 20
Stamford Suites
A room with a wooden floor, a black leather chair, a piano, and a large window with a view of a deck and trees.

2. Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
The price is CA $498
CA $1,361 total
includes taxes & fees
Aug 25 - Aug 26
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

3. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
The price is CA $139
CA $256 total
includes taxes & fees
Aug 24 - Aug 25
Welcome to Sweet Abby Rose!
A campfire with a wooden table and benches by a lake.

4. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (42 reviews)
"This is a beautiful property. Great location. And the hosts are very nice and very great in communicating everything. Loved staying there"
United States
Martina F.
The price is CA $293
CA $518 total
includes taxes & fees
Sep 17 - Sep 18
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern living room with a sofa, a coffee table, and a bar stool.

5. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is CA $200
CA $435 total
includes taxes & fees
Aug 24 - Aug 25
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

6. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (107 reviews)
"The property is clean and very nice"
United States
Nisse
The price is CA $245
CA $366 total
includes taxes & fees
Sep 13 - Sep 14
DUNE Fairfield Beach
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

7. Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"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 CA $200
CA $577 total
includes taxes & fees
Aug 19 - Aug 20
Modern Luxe 1BR Apt in Downtown Stamford
A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

8. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (16 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
The price is CA $194
CA $319 total
includes taxes & fees
Aug 20 - Aug 21
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A bedroom with a bed, a round mirror, a door, and wall decorations.

9. 2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
The price is CA $250
CA $319 total
includes taxes & fees
Aug 20 - Aug 21
2-bedroom apartmet No cleaning Fee
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

10. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is CA $197
CA $402 total
includes taxes & fees
Aug 24 - Aug 25
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

11. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (18 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is CA $294
CA $557 total
includes taxes & fees
Sep 15 - Sep 16
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

12. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is CA $292
CA $335 total
includes taxes & fees
Aug 19 - Aug 20
Guesthouse at Norwalk Inn
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, an oven, and a sink. There are two bar stools at the counter.

13. Modern Luxury 1BR Stamford Getaway

Modern Luxury 1BR Stamford Getaway
Downtown Stamford
10.0 out of 10, Exceptional, (1 review)
"The apartment is located in the hub bub of Stamford, a nice area very populated even in the evening where it feels safe. Apartment had all amenities that I needed. The host provided extra touches like a Keurig coffee pot stocked with Keurig cups and sugar. A washing machine and dryer were a plus as I like to pack only clean clothes. Bed was super comfortable. Modern design has a Zen vibe, great to decompress after travel. TV offered free movies that didn’t require my own subscription which...
United States
Debbie N.
The price is CA $276
CA $494 total
includes taxes & fees
Aug 29 - Aug 30
Modern Luxury 1BR Stamford Getaway
A bedroom with a bed, bedside tables, a mirror, and a patterned rug.

14. Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is CA $205
CA $383 total
includes taxes & fees
Sep 8 - Sep 9
Spacious Studio with Pool Table
A dining table set with blue bowls, gold cutlery, and yellow lemons.

15. Romantic Hide Out

Romantic Hide Out
Waterside
3.0 out of 10, (2 reviews)
"Check-in was at 3 PM and I was unable to reach the host until 11 PM that night to gain access to the property. They never sent anything in advance. It was the most miserable experience I have ever had."
United States
Cheryl H.
The price is CA $181
CA $375 total
includes taxes & fees
Sep 17 - Sep 18
Romantic Hide Out
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

16. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is CA $312
CA $564 total
includes taxes & fees
Aug 19 - Aug 20
Luxury NYC Home Game Room Free Parking
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

17. 2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
Greenwich
2.0 out of 10, (1 review)
"No lock on the entrance door so I had to use the bed frame against it to act as a barrier. I was woken up one morning by the host and had to leave the apartment ASAP because the housing inspector was there and she hid all my belongings that I couldn’t fully locate afterwards. "
United States
Ann E.
The price is CA $142
CA $402 total
includes taxes & fees
Aug 24 - Aug 25
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
A modern kitchen with a large island, white cabinetry, stainless steel appliances, and a view through large windows.

18. Private Country Getaway

Private Country Getaway
Bedford Hills
9.6 out of 10, Exceptional, (4 reviews)
"We had a busy and lovely weekend to attend and be part of my nieces wedding. The location was perfect and the property is beautiful. Kitchen was perfect for gathering in the morning and the great room was big and comfy for catching up! "
United States
Karin R.
The price is CA $1,040
CA $1,917 total
includes taxes & fees
Aug 25 - Aug 26
Private Country Getaway
A wooden staircase leading to a gazebo in a forested area with a metal railing.

19. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
8.0 out of 10, Very good, (5 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is CA $235
CA $312 total
includes taxes & fees
Sep 1 - Sep 2
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pound Ridge Hotel Reviews

Ethan Allen Hotel

Ethan Allen Hotel

8/10 Good
"Not able to pay in cash after being told it was okay."
Lori 2-night trip
Posted less than an hour ago
Ethan Allen Hotel

Find out more about Pound Ridge

Everything you need to know about Pound Ridge vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pound Ridge vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pound Ridge vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pound Ridge vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pound Ridge. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pound Ridge vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pound Ridge vacation rentals we have selected for you start as low as CA $206 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pound Ridge rentals

At Expedia, we put the best Pound Ridge vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pound Ridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pound Ridge vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pound Ridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a vacation rental in Pound Ridge?

Yes, there are vacation rentals in Pound Ridge close to Pound Ridge Library, or you can choose a secluded option if you're looking for extra privacy while you relax. 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?

Charming Home in Seaside: Visitors like this Pound Ridge vacation home rental. It is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Pound Ridge?

With 8 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?

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

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.