Pound Ridge holiday lettings

We found 379 holiday rentals — enter your dates for availability
Discover a selection of 9 homes and other holiday rentals in Pound Ridge that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you need and want for your stay, which might include Wi-Fi and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

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The natural setting of Pound Ridge is ready to explore

The area's history and museums are just some of the reasons to come on holiday to Pound Ridge. One of the city's many top draws is its sporting events. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Pound Ridge

Are you searching for attractions to see during your stay? Venture out of your cosy holiday rental and experience everything that Pound Ridge has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Norwalk Maritime Aquarium (11.2 mi / 18 km)
  • Chelsea Piers (11.2 mi / 18 km)
  • Putnam County Golf Course (15.6 mi / 25.1 km)
  • Centennial Golf Club (15.9 mi / 25.5 km)
  • Westchester Skating Academy (16 mi / 25.7 km)
  • Country Club of Fairfield (16.6 mi / 26.8 km)

Exploring the natural features in Pound Ridge

Whether you're an adventurous traveller or just want to take in the scenery, Pound Ridge is a great place to spend some time outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Mill River Park (10.8 mi / 17.4 km)
  • Cove Island Park (11.8 mi / 19 km)
  • Cummings Park Beach (12 mi / 19.4 km)
  • West Beach (12.1 mi / 19.4 km)
  • Calf Pasture Beach (12.7 mi / 20.4 km)
  • Hardscrabble Wilderness Area (12.9 mi / 20.7 km)

How to get to and around Pound Ridge

Fly into White Plains, NY (HPN-Westchester County), the closest airport, located 11.8 mi (18.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Danbury, CT (DXR-Danbury Municipal), which is 12.2 mi (19.7 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Pound Ridge?
Prices for holiday rentals in Pound Ridge vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Pound Ridge to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Pound Ridge holiday house rentals?
You can find great discounts on house rentals in Pound Ridge on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Pound Ridge ski resort rentals?
For those seeking ski resort rentals near Pound Ridge, the closest major ski area is in nearby New York State, particularly around the areas of Mount Kisco and Katonah. These towns offer a selection of holiday rentals that provide convenient access to the slopes. Many properties feature modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces for relaxation after a day on the mountain.

In the Pound Ridge area itself, visitors can find charming lodges and family homes that often come with amenities like fireplaces, hot tubs, and proximity to local dining options. The serene surroundings of Pound Ridge offer a beautiful backdrop for those looking to unwind, with properties frequently set in wooded areas or near scenic parks.

Travellers can also enjoy the local attractions, such as the Pound Ridge Reservation, which provides opportunities for hiking and nature walks, making these rentals ideal for both skiing enthusiasts and those looking to explore the natural beauty of the region.
What is the most popular type of holiday rental accomodation in Pound Ridge?
In Pound Ridge, holiday houses are the most popular type of holiday rental, with around 20 available throughout the area. These properties typically feature spacious layouts, including multiple bedrooms and large living areas, making them ideal for families or groups. Many holiday houses come with fully equipped kitchens, allowing guests to prepare their own meals, and often include outdoor spaces such as gardens or patios for relaxation and enjoying the natural surroundings.
Are there any family house rentals in Pound Ridge?
In Pound Ridge, New York, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The neighbourhood features spacious properties that often include multiple bedrooms, ample living areas, and fully equipped kitchens, allowing families to prepare their own meals together. Many of these homes also offer outdoor spaces such as gardens or patios, ideal for kids to play and for families to unwind after a day of exploring.

Visitors to Pound Ridge can enjoy the natural beauty of the surrounding area, including nearby parks and nature reserves, great for hiking and picnicking. The town's proximity to local attractions, including charming shops and restaurants, enhances the appeal for families seeking both adventure and relaxation.
Can I rent a holiday home with a pool or hot tub in Pound Ridge?
In Pound Ridge, there are several holiday homes available for rent that come equipped with pools or hot tubs. This picturesque area, known for its scenic landscapes and charming rural atmosphere, offers a variety of properties suited for relaxation and enjoyment. Travellers can expect amenities such as private swimming pools, hot tubs, and spacious outdoor areas, making them great for families or groups looking to unwind. Many of these rentals also feature fully equipped kitchens and comfortable living spaces, allowing for a home-like experience during your stay.
Can I find long-stay holiday rentals in Pound Ridge?
A long-stay holiday rental in Pound Ridge is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Pound Ridge?
In Pound Ridge, there are several pet-friendly house rentals available, offering a great escape in a picturesque setting. Many of these properties feature spacious layouts, fully equipped kitchens, and comfortable living areas, ideal for families and groups travelling with pets. Some homes may also include outdoor spaces such as fenced yards or patios where dogs can enjoy the fresh air.

The neighbourhood itself is known for its natural beauty, with nearby parks and trails great for walking your pet. The Pound Ridge Reservation, a local nature preserve, is a fantastic spot for experiencing the area's scenic landscapes while enjoying a leisurely hike with your furry friend.
Are there any remote work holiday rentals in Pound Ridge?
In Pound Ridge, there are approximately 20 remote work holiday rentals available, making it a suitable destination for those looking to combine work and leisure. Many of these properties come equipped with essential amenities for remote workers, including high-speed Wi-Fi, comfortable desks, and ergonomic chairs, ensuring a productive environment.

The area is known for its picturesque landscapes and tranquil atmosphere, which can provide a refreshing backdrop to your work routine. Nearby attractions include the scenic Pound Ridge Reservation, where you can enjoy nature walks and outdoor activities during breaks. Additionally, the charming local community offers quaint shops and restaurants, adding to the overall appeal of the area. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pound Ridge holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Pound Ridge with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Pound Ridge?
In Pound Ridge, holiday rentals typically come equipped with a range of popular amenities that enhance the comfort of guests. Visitors can expect properties to feature fully equipped kitchens, allowing for convenient meal preparation. Many rentals also include inviting decks or patios where guests can relax and enjoy the serene surroundings. Additionally, some accommodations boast porches or lanais, superb for sipping morning coffee or unwinding in the evening. Families will appreciate that several rentals provide children's books, making them a great choice for those travelling with young ones.
When is the best time to visit Pound Ridge for a holiday rental?
September is the most popular time to visit Pound Ridge, as the onset of autumn transforms the landscape into a vibrant tapestry of colours. This month marks the beginning of the peak season, which extends through November, attracting travellers keen to enjoy the stunning fall foliage and the crisp, refreshing air ideal for outdoor activities.

During this period, visitors can partake in various pursuits, from hiking the scenic trails in the nearby Ward Pound Ridge Reservation to exploring charming local shops and enjoying seasonal festivals. The mild temperatures, typically ranging from 10 to 20°C, provide a comfortable climate for sightseeing and leisurely strolls amidst nature's beauty.

For those seeking more affordable options, December can be a wonderful choice. While it falls into the low season, it offers a unique charm with the festive holiday spirit blanketing the area. Visitors can enjoy quieter surroundings, superb for cosy getaways and winter walks in the picturesque landscape.
How early should I book a Pound Ridge holiday rental?
Book your Pound Ridge holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Pound Ridge?
In Pound Ridge, visitors can enjoy the serene beauty of the area's natural landscapes and outdoor activities. A key attraction is the Pound Ridge Reservation, offering scenic hiking trails and opportunities for birdwatching, making it a great spot for nature enthusiasts. The nearby Ward Pound Ridge Reservation also features picnic areas and a variety of recreational activities.

For those interested in history, the historic Pound Ridge Community Church and the charming Town House are top landmarks that reflect the area's heritage. The local shops and eateries provide a quaint experience, often highlighting regional products and cuisine.
Can I change or cancel my Pound Ridge home rental booking on Vrbo?
To find Pound Ridge holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Pound Ridge holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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