Pawling holiday rentals

We found 261 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:18 Dec - 25 Dec

Balcony
Living area
Private kitchen
Dining
Exceptional
(8 reviews)

Nature & Luxury @Lavender Lake Est (Kosher optional)

Roxbury

8% off
AU$12,579
for 7 nights, 1 home
AU$1,797 per night
includes taxes & fees
Nature & Luxury @Lavender Lake Est (Kosher optional)
Private kitchen
Outdoor dining
Cozy library.
Well stocked eat-in kitchen with stainless appliances.
Exceptional
(122 reviews)

Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct

Danbury

8% off
AU$7,103
for 7 nights, 1 home
AU$1,015 per night
includes taxes & fees
Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct
Living area
Outdoor dining
Interior
Property grounds
Exceptional
(21 reviews)

Beautiful lake view home on Whaley Lake in Holmes, NY.

Holmes

8% off
AU$6,831
for 7 nights, 1 home
AU$976 per night
includes taxes & fees
Beautiful lake view home on Whaley Lake in Holmes, NY.
Exterior
Interior
Private kitchen
Property grounds
Exceptional
(34 reviews)

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Danbury

8% off
AU$10,961
for 7 nights, 1 home
AU$1,566 per night
includes taxes & fees
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Interior
Property grounds
Interior
Property grounds
Exceptional
(36 reviews)

Direct Lakefront Home on Lake Lillinonah with Elevator Access.

Brookfield

8% off
AU$7,162
for 7 nights, 1 home
AU$1,023 per night
includes taxes & fees
Direct Lakefront Home on Lake Lillinonah with Elevator Access.
Interior
Property grounds
Private kitchen
Dining
Exceptional
(7 reviews)

A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley

Holmes

8% off
AU$3,988
for 7 nights, 1 home
AU$570 per night
includes taxes & fees
A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
Interior
Family room
Exterior
Chef’s Kitchen
Exceptional
(21 reviews)

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Carmel

12% off
AU$6,604
for 7 nights, 1 home
AU$943 per night
includes taxes & fees
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Pool
Exterior detail
Property grounds
Private kitchen
Exceptional
(38 reviews)

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

New Fairfield

8% off
AU$3,513
for 7 nights, 1 apartment
AU$502 per night
includes taxes & fees
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

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)
  • Tymor Park (7.9 mi / 12.8 km)
  • Candlewood Lake (9.2 mi / 14.7 km)
  • Lake Mahopac (14.4 mi / 23.1 km)
  • Lake Lillinonah (14.6 mi / 23.4 km)
  • Tarrywile Park and Mansion (14.8 mi / 23.9 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, a popular area to stay is near the charming village centre. This location offers a delightful blend of small-town charm and accessibility to local attractions. You'll find a variety of properties available, ranging from quaint cottages to comfortable homes, making it a popular choice for visitors.In the village, you can explore the scenic beauty of the surrounding landscapes, particularly at the nearby Lakeside Park, which provides a serene setting for picnics and leisurely walks. Additionally, the Pawling Historical Society offers intriguing insights into the area's rich history, making it a worthwhile stop for those keen on local culture.Another great neighbourhood to consider is around the Appalachian Trail entrance, which is superb for outdoor enthusiasts. With numerous hiking trails and stunning views, it's a fantastic spot for those looking to immerse themselves in nature. The availability of properties in this area caters to both families and solo travellers seeking a peaceful retreat.
What is the most popular type of holiday rental accomodation in Pawling?
In Pawling, holiday houses are the most popular type of holiday rental, with several available throughout the area. These properties typically offer spacious rooms, featuring multiple bedrooms and fully equipped kitchens, ideal for families or groups looking to enjoy a longer stay. Many holiday houses come with outdoor spaces such as gardens or patios, great for relaxing after a day of exploring the picturesque surroundings.
Are there any family house rentals in Pawling?
In Pawling, New York, there are some family-friendly house rentals available, making it a lovely choice for those travelling with children. Many properties in this charming town feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can play safely.The locale is also close to top attractions such as the scenic Appalachian Trail, which offers excellent hiking opportunities, and the quaint downtown area with its shops and restaurants, great for family outings. Visitors can expect amenities like Wi-Fi and comfortable sleeping arrangements that cater to larger groups or families.
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 come with pools or hot tubs. This picturesque town, located in the scenic Hudson Valley, offers a tranquil retreat for those looking to unwind. Many of the rental properties feature private outdoor pools, hot tubs, and spacious patios, making them ideal for relaxation and family gatherings.Travellers can expect amenities such as fully equipped kitchens, expansive living areas, and outdoor dining spaces, superb for enjoying meals al fresco. The natural beauty of the surrounding area provides opportunities for hiking, biking, and exploring local parks, adding to the appeal of a holiday in Pawling.
Are there any remote work holiday rentals in Pawling?
In Pawling, New York, there are several remote work-friendly holiday rentals available, making it an excellent choice for those looking to blend work and leisure. Many of these properties are equipped with dedicated office spaces or bookable units, allowing for a productive environment. Internet access is typically provided through a third-party service, ensuring reliable connectivity for remote work needs.The area itself is quite charming, with its picturesque landscapes and proximity to outdoor activities. Visitors can enjoy local attractions such as the Appalachian Trail for hiking or the quaint shops and cafes in the town centre. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Pawling?
In Pawling, popular rental amenities include balconies, which provide a lovely spot for enjoying the outdoors, and coffee and tea makers for a convenient morning routine. Many properties also feature decks or patios, ideal for relaxing outside after a day of exploring. Electric car charging stations are available for eco-conscious travellers, and fireplaces can be found in some rentals, offering a cosy atmosphere during cooler months.
When is the best time to visit Pawling for a holiday rental?
April is the most popular month to visit Pawling, marking the height of the spring season when nature bursts into bloom and the weather becomes pleasantly mild. From March to May, the area attracts visitors eager to enjoy outdoor activities such as hiking, cycling, and exploring the charming local shops and eateries.During this period, temperatures typically range from 5 to 20 degrees Celsius, providing a comfortable climate for sightseeing and leisurely strolls through the picturesque town and surrounding parks. The blossoming landscapes create a stunning backdrop for those looking to soak in the beauty of the Hudson Valley.If you're considering a more economical trip, December offers a unique charm with fewer crowds. This quieter month allows you to enjoy the serene winter landscapes and local holiday festivities, making it a wonderful time for a peaceful retreat.Ultimately, your ideal time to visit Pawling will depend on whether you're drawn to the vibrant energy of springtime activities or the tranquil beauty of winter's embrace.
What are the top attractions in Pawling?
In Pawling, visitors can enjoy a variety of attractions that highlight the area's natural beauty and historical significance. The scenic Appalachian Trail runs nearby, offering excellent hiking opportunities with picturesque views of the surrounding landscapes. The charming village centre features local shops, cafes, and restaurants that reflect the town's quaint atmosphere.The Pawling Nature Reserve is a highlight for outdoor enthusiasts, providing trails for hiking and birdwatching, as well as the tranquil waters of the Housatonic River for fishing. Additionally, the historic Pawling Train Station, part of the Metro-North Railroad, is an important landmark that connects the town to New York City, making it a convenient spot for day trips.Art lovers may appreciate the nearby Lakeside Park, which often hosts community events and outdoor concerts, creating a vibrant local culture. For those interested in history, the John Kane House offers insights into the region's past and is a lovely place to explore.
Are all fees included in the Pawling holiday homes prices shown on Stayz?
Stayz 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 Pawling holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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 Pawling holiday homes?
You can find great discounts on holiday homes in Pawling on Stayz, 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 Pawling holiday home booking on Stayz?
To find Pawling holiday rentals with free cancellation, just use Stayz'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, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pawling?
A long-stay holiday home 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 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 Stayz?
Stayz'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 Pawling holiday home?
Book your Pawling 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pawling?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pawling to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.