Pawling holiday lettings

We found 254 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Pawling to find one that's perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you expect for your stay, which might include Wi-Fi and a hot tub. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Pawling

Showing deals for:13 Mar - 20 Mar

Image gallery for ENJOY THE HOLIDAY SEASON AT THIS COZY, WARM, LOG CABIN IN THE COUNTRY! BOOK NOW!

Interior
10 out of 10, Exceptional, (59 reviews)
Exceptional
(59 reviews)

ENJOY THE HOLIDAY SEASON AT THIS COZY, WARM, LOG CABIN IN THE COUNTRY! BOOK NOW!

Dover Plains, NY

16% off
Price is £7,763
for 7 nights, 1 cabin
£1,109 per night
includes taxes & fees
ENJOY THE HOLIDAY SEASON AT THIS COZY, WARM, LOG CABIN IN THE COUNTRY! BOOK NOW!

Find spaces that suit your style

Historical Pawling will entice you

Enjoy the history and other features of Pawling. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Pawling

Are you hoping to find attractions to visit in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Pawling has to offer. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Thunder Ridge Ski Resort (3.9 mi / 6.3 km)
  • Putnam County Golf Course (14.5 mi / 23.4 km)
  • SplashDown Beach (15.7 mi / 25.3 km)
  • Hopkins Vineyard (16.2 mi / 26.1 km)
  • Millbrook Vineyards and Winery (19.7 mi / 31.8 km)
  • Beekman Golf Course (9.2 mi / 14.8 km)

Exploring the natural features in Pawling

Whether you're an active traveller or just want to spend some time taking in the scenery, Pawling is a great spot to appreciate mother nature. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Whaley Lake (3.1 mi / 5 km)
  • Candlewood Lake (9.2 mi / 14.7 km)
  • Lake Mahopac (14.4 mi / 23.1 km)
  • Tarrywile Park and Mansion (14.8 mi / 23.9 km)
  • Steep Rock Preserve (14.9 mi / 24 km)
  • Lake Waramaug State Park (15.2 mi / 24.5 km)

Travelling to and around Pawling

The nearest airport is in Danbury, CT (DXR-Danbury Municipal), located 14.4 mi (23.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Oxford, CT (OXC-Waterbury - Oxford), which is 24.7 mi (39.7 km) away.

If you'd rather travel by train, you can make your way to Appalachian Trail.

Frequently asked questions

What is the best area to stay in Pawling when booking a holiday rental?
When considering a holiday rental in Pawling, New York, the best area to stay in is the charming downtown district. This picturesque neighbourhood is not only scenic but also offers a vibrant atmosphere with a variety of quaint shops, delightful cafes, and restaurants. One of the top attractions in this area is the Pawling Train Station, a beautifully restored historic site that adds character to the town. Additionally, the nearby Lakeside Park provides a lovely setting for leisurely strolls, picnics, or simply enjoying the natural beauty of the landscape.
How much does it cost to rent a holiday home in Pawling?
Prices for holiday rentals in Pawling 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 Pawling 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 Pawling holiday house rentals?
You can find great discounts on house rentals in Pawling 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.
What is the most popular type of holiday rental accomodation in Pawling?
In Pawling, holiday houses are the most popular type of rental accommodation, with several available throughout the area. These properties typically feature spacious interiors, multiple bedrooms, and fully equipped kitchens, providing a comfortable home-like atmosphere for families or groups. Many holiday houses also come with outdoor spaces such as gardens or patios, allowing guests to enjoy the scenic views and fresh air after a day of exploring the charming town and its surrounding nature.
Are there any family house rentals in Pawling?
In Pawling, New York, there are several family-friendly house rentals available, making it an appealing choice for those travelling with children. This charming town offers a variety of properties, many of which feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can play and explore.

Visitors can enjoy amenities such as comfortable bedrooms, Wi-Fi, and sometimes even game rooms or private yards, enhancing the overall experience for families. The locale is close to scenic spots like the Appalachian Trail, great for hiking and outdoor adventures, and the quaint downtown area offers shops and eateries that cater to all tastes.
Can I rent a holiday home with a pool or hot tub in Pawling?
In Pawling, New York, there are several holiday homes available for rent that feature pools and hot tubs. This charming town, located in the Hudson Valley, offers a relaxing retreat for travellers looking to unwind. Many of the rentals come with private pools, outdoor hot tubs, and well-appointed patios, superb for enjoying the scenic views that the area has to offer.
Can I find long-stay holiday rentals in Pawling?
A long-stay holiday rental in Pawling 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 any remote work holiday rentals in Pawling?
In Pawling, New York, there are several holiday rentals suitable for remote work. Many of these properties offer dedicated office spaces and reliable Wi-Fi, providing an ideal environment for productivity. You can expect a variety of amenities that cater to remote workers, including comfortable workstations and tranquil settings to help maintain focus. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pawling holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Pawling 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 Pawling?
In Pawling, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals. Many properties also feature outdoor spaces such as patios or decks, superb for enjoying the serene surroundings. Additionally, some rentals come with pools, providing a refreshing option for relaxation during warmer months.
When is the best time to visit Pawling for a holiday rental?
The best time to visit Pawling for a holiday rental is during the peak season, which runs from March to May, with April being particularly popular. This vibrant period attracts travellers keen on enjoying the natural beauty of the Hudson Valley as the landscape comes alive with spring blooms. The mild temperatures, typically reaching the low 20s Celsius, create an inviting environment for outdoor activities such as hiking and cycling, allowing visitors to fully appreciate the scenic trails and lush parks nearby.

April, in particular, offers a delightful atmosphere with numerous local events and festivals that celebrate the season, making it an excellent choice for those looking to immerse themselves in the community spirit. The charming town of Pawling also has quaint shops and cafés that are great for leisurely afternoons after a day of exploration.

For those considering a budget-friendly option, visiting Pawling in December can provide a great experience. While this month is generally quieter and outside the main tourist season, it offers a lovely winter wonderland atmosphere, ideal for those who enjoy a peaceful retreat. The holiday decorations and local festivities can add a special touch to your stay, great for cosy getaways.
How early should I book a Pawling holiday rental?
Book your Pawling 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.
Can I change or cancel my Pawling home rental booking on Vrbo?
To find Pawling 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 Pawling 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.

More holiday ideas