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

Pound Ridge Holiday Rentals

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Our top choices for Pound Ridge holiday rentals

1. 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 NZ$313
includes taxes & fees
11 Aug - 12 Aug
Welcome to Sweet Abby Rose!

2. 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 NZ$536
includes taxes & fees
13 Aug - 14 Aug
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

3. 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 NZ$1,301
includes taxes & fees
25 Aug - 26 Aug
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

4. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (157 reviews)
"The front desk gentleman that checked us in was excellent!!"
United States
Selena
The price is NZ$275
includes taxes & fees
16 Aug - 17 Aug
Stamford Suites

5. 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
7.6 out of 10, Good, (4 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 NZ$262
includes taxes & fees
11 Aug - 12 Aug
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

6. 2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
The price is NZ$392
includes taxes & fees
11 Aug - 12 Aug
2-bedroom apartmet No cleaning Fee

7. 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 NZ$392
includes taxes & fees
11 Aug - 12 Aug
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

8. 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 NZ$492
includes taxes & fees
11 Aug - 12 Aug
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

9. 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 NZ$600
includes taxes & fees
13 Aug - 14 Aug
Modern Luxury 1BR Stamford Getaway

10. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (104 reviews)
"Staff is excellent very clean and comfortable. Nice pla e with great beach access!"
United States
Stacie
The price is NZ$529
includes taxes & fees
17 Aug - 18 Aug
DUNE Fairfield Beach

11. 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 NZ$489
includes taxes & fees
8 Sept - 9 Sept
Spacious Studio with Pool Table

12. 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 NZ$498
includes taxes & fees
24 Aug - 25 Aug
Romantic Hide Out

13. 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 NZ$697
includes taxes & fees
19 Aug - 20 Aug
Modern Luxe 1BR Apt in Downtown Stamford

14. 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 NZ$639
includes taxes & fees
8 Sept - 9 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

15. 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 NZ$487
includes taxes & fees
11 Aug - 12 Aug
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

16. '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 reviews)
"Great stay!"
United States
Ann S.
The price is NZ$617
includes taxes & fees
24 Aug - 25 Aug
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

17. Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Carmel
9.4 out of 10, Exceptional, (10 reviews)
"Such a lovely cabin - so many details to make for an incredible stay. Amazing location - lake, mountains! Wylda was wonderful."
United States
Clare
The price is NZ$383
includes taxes & fees
13 Aug - 14 Aug
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

18. The Hideaway

The Hideaway
Brewster
10.0 out of 10, Exceptional, (8 reviews)
"Nice, clean, comfortable place to stay. Beautiful, convenient setting. Will look to come back again some day for sure. "
United States
Kenneth M.
The price is NZ$524
includes taxes & fees
1 Sept - 2 Sept
The Hideaway

19. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is NZ$600
includes taxes & fees
14 Aug - 15 Aug
Elegant Hideaway with Free Parking

20. Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
10.0 out of 10, Exceptional, (2 reviews)
"A wonderful place. Beds where comfortable. Would most definitely come back there again. Quiet and safe atmosphere. Not far from the highway. Host was very nice."
United States
Lisa J.
The price is NZ$505
includes taxes & fees
11 Aug - 12 Aug
Zen, Spacious & Comfy 2 bed, Lux beds
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

Find out more about Pound Ridge

Everything you need to know about Pound Ridge holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pound Ridge holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pound Ridge holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pound Ridge holiday rentals we have selected for you start as low as NZ$262 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 holiday 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 holiday.

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 holiday rental in Pound Ridge?

Yes, there are holiday rentals in Pound Ridge close to Pound Ridge Library, or you can select a more secluded option if you're looking for a relaxing stay. Pound Ridge is known for its sporting events and museums.

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

Charming Home in Seaside: This holiday home rental outside of Pound Ridge 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 that you can cook with friends or family.

How many holiday rentals will I find in Pound Ridge?

With 8 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Pound Ridge Library and Caramoor Center for Music and the Arts.

What are holiday rentals like in Pound Ridge?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pound Ridge. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.