Pound Ridge holiday homes

We found 364 holiday rentals — enter your dates for availability
Discover a selection of 8 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.

Holiday rentals with weekly discounts – Pound Ridge

Showing deals for:25 Dec - 1 Jan

Interior
Private kitchen
Room
Exterior
Exceptional
(6 reviews)

Darien family home on a Cul de Sac with pond.

Darien

8% off
NZ$11,294
for 7 nights, 1 home
NZ$1,613 per night
includes taxes & fees
Darien family home on a Cul de Sac with pond.
Living area
Marina
Outdoor dining
Interior
Wonderful
(16 reviews)

<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽

Stamford

7% off
NZ$2,609
for 7 nights, 1 apartment
NZ$373 per night
includes taxes & fees
<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽
Private kitchen
Children’s area
Children’s area
Outdoor dining
Exceptional
(25 reviews)

Stylish downstairs apt. Walk to town, train, & beach ferry! Off-street parking.

Greenwich

8% off
NZ$5,823
for 7 nights, 1 home
NZ$832 per night
includes taxes & fees
Stylish downstairs apt. Walk to town, train, & beach ferry! Off-street parking.
Living area
Living area
Room
Private kitchen
Very good
(13 reviews)

❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC

Stamford

7% off
NZ$2,766
for 7 nights, 1 apartment
NZ$395 per night
includes taxes & fees
❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC
Room
Interior
Interior
Interior
Exceptional
(10 reviews)

The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC

Stamford

5% off
NZ$1,796
for 7 nights, 1 apartment
NZ$257 per night
includes taxes & fees
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC
Private kitchen
Interior
Interior
Dining
Exceptional
(9 reviews)

Luxurious 3BR/2BA Modern Haven Downtown Stamford

Stamford

8% off
NZ$7,202
for 7 nights, 1 apartment
NZ$1,029 per night
includes taxes & fees
Luxurious 3BR/2BA Modern Haven Downtown Stamford

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    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Pound Ridge

  • Nature Reserves: Explore stunning landscapes at the Ward Pound Ridge Reservation, perfect for hiking and picnicking.
  • Pound Ridge Museum: Discover local history and culture in this charming museum showcasing the area’s heritage.
  • Pound Ridge Golf Club: Enjoy a round of golf at this picturesque course set among rolling hills.
  • Quaint Villages: Stroll through the charming nearby area of Long Ridge, filled with unique shops and eateries.
  • Family-Friendly Activities: Engage in various outdoor adventures ideal for families seeking fun and excitement.

Top attractions near Pound Ridge

Pound Ridge, New York, is perfect for outdoor enthusiasts and those seeking a romantic getaway. Explore stunning nature reserves and urban parks, or visit local attractions like the Pound Ridge Museum and the Pound Ridge Golf Club. Families will enjoy outings at the Ward Pound Ridge Reservation, making it an ideal destination for culture and adventure alike. Discover the charm of this picturesque area and create lasting memories on your holiday.

  • The Glass House: A stunning museum set in a serene landscape, showcasing modern architecture and art. Its transparent design allows for a unique connection with nature, making each visit a reflective experience.
  • Lockwood-Mathews Mansion: A magnificent historic house that embodies the grandeur of the Gilded Age. Visitors can explore its exquisite interiors and learn about its fascinating history, offering a glimpse into a bygone era.
  • Caramoor Center for Music and the Arts: An enchanting arts centre surrounded by beautiful gardens, renowned for its exceptional music performances. It provides a delightful atmosphere for enjoying various artistic events throughout the year.

Things to do recommended for couples

For a romantic getaway in Pound Ridge, indulge in the luxury vibes at the Greenwich Polo Club, only 9.7km away. Then, unwind together at the Hand & Stone Massage and Facial Spa, 16.1km away, where wellness and relaxation await you both.

Things to do recommended for families

Your family will love exploring Dorothy Heroy Park for relaxation, enjoying sports at Mead Memorial Park, and unwinding at Scofieldtown Park. Each spot offers a delightful blend of wellness and fun, making Pound Ridge a fantastic destination for a memorable family holiday.

Things to do recommended for groups

Groups visiting Pound Ridge can enjoy a night out at the Ridgefield Playhouse for some culture and entertainment, hit the Stamford Town Center for shopping and family fun, or challenge each other on the greens at the nearby Stanwich Club for a sporty outdoor experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Pound Ridge

If you're heading off on an adventure with a group, family, or even your pets, or if you're considering an extended stay, it's important to filter your options according to your specific needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Pound Ridge with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor areas for group get-togethers. Luckily, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Pound Ridge with young kids: Taking a trip with little ones can be quite a task. It’s important to prioritise their comfort and safety, along with suitable amenities for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are great for families.
  • Taking your pets with you to Pound Ridge: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pound Ridge: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filter, you can effortlessly discover and save on long-term rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Pound Ridge

Pound Ridge, New York, offers a delightful escape for those seeking outdoor adventures and romantic scenery. Nestled among rolling hills, this charming town invites visitors to explore its rich history and family-friendly atmosphere. Stroll through the picturesque landscapes, enjoy a day in the lush parks, or discover the quaint charm of nearby Long Ridge. With its welcoming vibe and beautiful surroundings, Pound Ridge is the perfect spot for a memorable holiday experience.

  • Stamford: Stamford is a vibrant city located 17.7km from Pound Ridge, offering a delightful mix of family-friendly activities and urban experiences. Visitors can explore a variety of shopping areas, catch a performance at the local theatre, and enjoy educational attractions. The city's modern square and tourist precinct serve as popular gathering spots, where you can find a range of dining options and entertainment venues. Stamford is perfect for those looking to enjoy both outdoor adventures and the hustle and bustle of city life.
  • Norwalk: Norwalk, also situated 17.7km from Pound Ridge, is a fantastic destination for families and outdoor enthusiasts alike. The city is known for its beautiful beaches, including family-friendly options, and offers various recreational activities such as skiing in the winter months. With a strong focus on education and a number of shopping areas, Norwalk provides a well-rounded travel experience. Don’t miss the chance to visit its historic sites, which add cultural depth to your exploration.
  • White Plains: Located 25.7km from Pound Ridge, White Plains is a bustling city that caters to families, business travellers, and culture seekers. The city boasts an array of shopping areas, a thriving arts centre, and a lively theatre scene, making it an ideal spot for both leisure and business visits. Key attractions include the modern square and tourist precinct, where visitors can enjoy a vibrant atmosphere filled with shops and eateries. White Plains offers a unique blend of urban sophistication and family-oriented activities.

Best time to go to Pound Ridge

If you're planning a trip to Pound Ridge, it's a good idea to check both the weather and property rates. The warmest month is July.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.6°F (-0.8°C)Light RainMostly SunnySlightly Low
February32.0°F (0.0°C)Light RainMostly SunnyAverage
March38.7°F (3.7°C)Light RainMostly SunnyAverage
April48.9°F (9.4°C)Light RainMostly SunnySlightly High
May59.0°F (15.0°C)Light RainMostly SunnyAverage
June67.8°F (19.9°C)Light RainMostly SunnyAverage
July74.7°F (23.7°C)Light RainMostly SunnySlightly High
August73.4°F (23.0°C)Light RainMostly SunnySlightly Low
September66.7°F (19.3°C)Light RainMostly SunnySlightly High
October56.7°F (13.7°C)Light RainMostly SunnyAverage
November45.3°F (7.4°C)Light RainMostly SunnyAverage
December36.9°F (2.7°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can change quite a bit. Also, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that suits your budget, make use of our filters to search by price, location, and type of accommodation. Happy travels.

Vrbo Trips: Effortless planning

Vrbo's clever Trip Board offers you a convenient way to plan your next getaway, pick up where you last stopped, or keep track of your travel arrangements. You can easily find the properties you've saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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)
  • Rye Playland (17.5 mi / 28.2 km)
  • Stanwich Club (6.3 mi / 10.1 km)
  • Grand Prix New York / Spins Bowl (7.4 mi / 12 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:

  • Lucius Pond Ordway / Devil's Den Preserve (9.5 mi / 15.3 km)
  • Cove Island Park (11.8 mi / 19 km)
  • West Beach (12.1 mi / 19.4 km)
  • Tarrywile Park and Mansion (13.4 mi / 21.6 km)
  • Compo Beach (13.6 mi / 21.9 km)
  • Rogers Park (14 mi / 22.6 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

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.
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 Bookabach.
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.
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.
Are all fees included in the Pound Ridge holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Pound Ridge holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Pound Ridge holiday homes?
You can find great discounts on holiday homes in Pound Ridge on Bookabach, 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.
Can I change or cancel my Pound Ridge holiday home booking on Bookabach?
To find Pound Ridge holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Pound Ridge?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Pound Ridge holiday home?
Book your Pound Ridge holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pound Ridge?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Pound Ridge to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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