Pound Ridge Holiday Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Pound Ridge

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Smart TV, computer monitors, printers

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

9.4 out of 10, Exceptional, (3)
"I spent 2 serene weeks here and hope to return some day! With modern creature comforts in the kitchen, the rest of this home is very rustic. If you are looking for peace and quiet, and are into drawing, cooking or reading books to the sounds of trees rustling and water flowing across the street, you will be in heaven here. For summer months, note that there is only a small portable AC unit in the sunroom. There are several fans and it was manageable in early summer, but I imagine it is quite...
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Stamford Suites
Exterior

Stamford Suites

2.5 star property
6.8 out of 10, (772)
"It was in walking distance of the event we were going to."
The price is HK$1,645
HK$1,891 total
includes taxes & fees
25 Dec - 26 Dec
Stamford Suites
DUNE Fairfield Beach
Private beach nearby, sun-loungers, beach umbrellas, beach towels

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (43)
"Good communication and easy to check in and out. The blow dryer was broken. The internet kept going out; I dropped off a work call and had a hard time getting back on. Please fix the WiFi."
DUNE Fairfield Beach
Global Luxury Suites White Plains
Reception

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (27)
"Great location, friendly people, great apartment "
Global Luxury Suites White Plains
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
Interior

Welcome to Villa Seabird, Luxury Escape on Long Island Sound

10.0 out of 10, Exceptional, (9)
"This was amazing Thanksgiving with my family. The house is amazing Jon was amazing host and his recommendation for food made you feel like million dollars. Can not thank you enough to share your beautiful home with us and see you in the summer."
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Terrace/patio

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (115)
"Enjoyed the theater room and the comfortable bed"
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Luxury Designer 2 bedroom+office/3bed vacation home.
Miscellaneous

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

9.4 out of 10, Exceptional, (15)
"Great little spot. Central enough to get everywhere we needed to. Walked to restaurants and to a concert (about 30 minutes). Host had some treats for us when we checked in. Apartment was clean and spacious. Felt comfortable walking around the neighborhood "
The price is HK$1,228
HK$3,347 total
includes taxes & fees
1 Jan - 2 Jan 2025
Luxury Designer 2 bedroom+office/3bed vacation home.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Outdoor dining

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (26)
"The view in the fall was amazing! So relaxing to sit and watch the lake while having our coffee. The owners are amazing. Everything we needed and more. Plenty of room for the family or even if multiple families stayed. Would stay here again!"
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Westport Paradise With Every Amenity!
Outdoor pool, a heated pool

Westport Paradise With Every Amenity!

10.0 out of 10, Exceptional, (23)
"We had such a nice stay at Mark and Sarah’s. Check in was so easy and they were very attentive to anything we needed. The property and apartment are beautiful, it was so nice waking up and seeing all the trees and it was so quiet. We will definitely be back and stay when we are visiting our daughter at Fairfield."
The price is HK$3,807
HK$5,488 total
includes taxes & fees
19 Dec - 20 Dec
Westport Paradise With Every Amenity!
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Miscellaneous

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 HK$3,877
HK$7,085 total
includes taxes & fees
3 Jan - 4 Jan 2025
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
Point of interest

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

8.6 out of 10, Excellent, (4)
"The location of Ms. Jay's place is unbeatable! My group and I were in town for an event in the Total Mortgage Arena. The drive was 5 minutes max! Ms. Jay is great with communication. She was always available for any questions. The apartment is very homey, cozy and comfortable. Very nicely decorated and it has everything you might need. (We would just recommend some mirrors in the bedrooms). The place is next to a very busy street which there is always a lot of noise, especially at night. One...
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Fridge, microwave, oven, stovetop

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

9.8 out of 10, Exceptional, (17)
"This place was super clean and exactly as described. "
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Cheerful 4 bedrooms residential house.
Fridge, microwave, dishwasher, coffee/tea maker

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (25)
"Great communication and accommodations from the host. We were in town for a concert and the location couldn't have been better! Would recommend this stay for anyone looking within the area."
Cheerful 4 bedrooms residential house.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (75)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Exterior

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

10.0 out of 10, Exceptional, (78)
"Very large house just like the photos. Host is present and responsive. We had the entire property to ourselves. Nice yard for some whiffle ball and outdoor activities. Swimming is possible at the public lake access which is about a mile away or so. Overall, a very nice stay at a very nice property. We were 10 adults (friends weekend) and fit just fine. "
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Guesthouse at Norwalk Inn
Private kitchen

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"Great space would be better if there were kuerig cups to go with the machine in the kitchen"
The price is HK$2,146
HK$2,468 total
includes taxes & fees
22 Dec - 23 Dec
Guesthouse at Norwalk Inn
The Safe House - High Tech Apt #2 - 3 Beds
Beach

The Safe House - High Tech Apt #2 - 3 Beds

9.6 out of 10, Exceptional, (35)
"Enjoyed my second stay at the Safe House. Plenty of space, great proximity to Greenwich downtown."
The price is HK$917
HK$1,756 total
includes taxes & fees
14 Jan - 15 Jan 2025
The Safe House - High Tech Apt #2 - 3 Beds
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Fridge, microwave, oven, stovetop

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (20)
"Long weekend with family to participate in a christening in the Bronx. Place was clean and comfortable. Location was very convenient. Only change I would request would be extra blankets. Otherwise would stay again. "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
The Safe House - High Tech Apt #3 - 4 beds
Beach

The Safe House - High Tech Apt #3 - 4 beds

9.8 out of 10, Exceptional, (41)
"Property worked out great for us"
The price is HK$785
HK$1,585 total
includes taxes & fees
19 Dec - 20 Dec
The Safe House - High Tech Apt #3 - 4 beds
Cozy secret apartment with free parking in Yonkers
1 bedroom, desk, iron/ironing board, travel cot

Cozy secret apartment with free parking in Yonkers

9.4 out of 10, Exceptional, (3)
"Great nice and safe, nice area"
The price is HK$1,010
HK$1,709 total
includes taxes & fees
10 Jan - 11 Jan 2025
Cozy secret apartment with free parking in Yonkers
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.
Don't see what you're looking for?
See all available properties in Pound Ridge
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Pound Ridge you may be interested in

Amsterdam Hotel
Front of property

Amsterdam Hotel

2.0 star property
8.4 out of 10, Very good, (1518)
"Convenient to the train station, affordable rates. "
The price is HK$777
HK$901 total
includes taxes & fees
19 Dec - 20 Dec
Amsterdam Hotel
Sleepy Hollow Hotel
Lobby

Sleepy Hollow Hotel

3.5 star property
6.6 out of 10, (1001)
"We stayed during the Halloween parade and related events. The property is very walkable, about twenty minutes from the downtown area. The hills might be treacherous for those with strollers or wheelchairs, but it was very accessible for those who can walk comfortably. Parking at the hotel was very accommodating, and that was useful as parking downtown seemed like a nightmare. We got one of the larger, premium rooms, and it was pleasant. Bathrooms were very nice. "
The price is HK$984
HK$1,126 total
includes taxes & fees
5 Jan - 6 Jan 2025
Sleepy Hollow Hotel
Hampton Inn & Suites Yonkers
Exterior

Hampton Inn & Suites Yonkers

2.5 star property
8.2 out of 10, Very good, (1061)
"Perfect stay as we have always experienced. Only thing I would say is now $15 for parking is a little absurd. "
The price is HK$852
HK$1,003 total
includes taxes & fees
2 Jan - 3 Jan 2025
Hampton Inn & Suites Yonkers
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.

Frequently asked questions

Can I find a holiday rental in Pound Ridge?

Yes, there are holiday rentals close to the most popular sights in Pound Ridge, 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?

Lower Lvl Private 2BR/1BA Family/Pet Friendly: This holiday home rental outside of Pound Ridge offers a patio, a terrace and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals will I find in Pound Ridge?

With 7 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 The Glass House and Stamford Museum and Nature Center.

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.