Pawling vacation rentals

We found 254 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Pawling to find one that's perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include WiFi and a washer and dryer, What you'll find is a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Pawling

Showing deals for:Apr 17 - Apr 24

Image gallery for Nature & Luxury @Lavender Lake Est (Kosher optional)

Pool
10 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Nature & Luxury @Lavender Lake Est (Kosher optional)

Roxbury

13% off
Price is $1,155
$8,086 for 7 nights
All fees included
Nature & Luxury @Lavender Lake Est (Kosher optional)

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Find out more about Pawling

Why visit Pawling

  • Scenic Outdoor Escapes: Enjoy breathtaking landscapes with national parks and serene lakes perfect for hiking and picnicking.
  • Charming Village Atmosphere: Explore Pawling's quaint village, filled with friendly locals and a welcoming ambiance.
  • Family-Friendly Activities: Discover various attractions designed for families, ensuring fun for all ages.
  • Cozy Accommodations: Choose from private homes, cottages, and apartments that provide comfort and unique experiences.
  • Cultural Enrichment: Immerse yourself in local culture by visiting the community library and participating in local events.

Popular types of accommodation in Pawling

If you're exploring vacation rentals in Pawling, you're in for a treat. Our most popular accommodations include houses, cozy cottages, and comfortable apartments. Whether you’re looking for Pawling apartments or vacation homes, you’ll find options that offer available parking and select amenities to enhance your stay. Discover the perfect retreat that meets your needs and enjoy a memorable getaway in this charming area.

  • Houses: The top choice for visitors, these spacious and well-equipped homes offer a perfect setting for families or groups seeking comfort and privacy.
  • Cottages: These quaint and charming accommodations provide a cozy atmosphere, ideal for a romantic getaway or a peaceful retreat.
  • Apartments: Conveniently located, apartments offer modern amenities and easy access to local attractions, perfect for solo travelers or couples.
  • Cabins: Nestled in nature, these rustic hideaways are great for those looking to enjoy the great outdoors and unwind.
  • Villas: Luxurious and spacious, villas provide an upscale experience for those wanting extra comfort and style during their stay.**

Top attractions in and around Pawling

Pawling, New York, is a picturesque destination perfect for outdoor enthusiasts and romantic getaways. Visitors can explore stunning national parks, enjoy serene lakes, and immerse themselves in local culture at the library. With a variety of attractions catering to families and those seeking unique experiences, Pawling promises a memorable vacation filled with scenic beauty and enriching activities.

  • Candlewood Lake: Located 9 miles from Pawling, Candlewood Lake is a picturesque destination perfect for a romantic getaway. Enjoy its beautiful beach, stunning scenery, and outdoor activities like boating and fishing, making it an ideal spot to relax and unwind in nature.
  • John Kane House: Situated within Pawling, the John Kane House is a charming historic site that immerses visitors in local culture. Explore its rich history and architecture, offering a glimpse into the past and the community's heritage.
  • Squantz Pond State Park: Just 8 miles from Pawling, Squantz Pond State Park is a haven for adventure seekers. With scenic trails and outdoor activities, it's perfect for hiking, swimming, and enjoying the breathtaking views of the surrounding landscape.

Things to do recommended for couples

Ready for a romantic getaway in Pawling? Hit the slopes at Thunder Ridge Ski Resort, enjoy a concert at the Danbury Music Centre, or savor exquisite wines at Hopkins Vineyard. Each experience offers a unique blend of adventure and romance, perfect for couples looking to connect.

Things to do recommended for families

Families will have a blast at Fun Central, an exciting arcade and adventure zone located 16 miles from Pawling. With its thrilling games and family-friendly atmosphere, it's the perfect spot for memorable fun and bonding time together.

Things to do recommended for groups

In Pawling, your group can visit the Stormville Airport Antique Show & Flea Market for unique finds, explore the Danbury Fair Mall for shopping and entertainment, or enjoy a round of golf at the Centennial Golf Club, perfect for outdoor enthusiasts.

*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 Pawling

If you're traveling with a group, your family, bringing pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Pawling with a group: Think about how many bedrooms you require, as well as features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Pawling with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Pawling: For many families, a trip isn't truly complete without their furry companions. If this resonates with you, take a look at Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pawling: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can easily discover and save on monthly rentals. Don't forget to consider features like parking, a spacious kitchen, or a private pool in your search as well.

Where to stay near Pawling

Pawling, New York, offers a charming blend of scenic beauty and historical richness, perfect for a romantic and peaceful getaway. Explore the quaint village, where friendly locals create a welcoming atmosphere. Nearby, discover family-friendly activities and budget-friendly destinations, all set against a backdrop of stunning landscapes. Whether you're seeking relaxation or adventure, Pawling and its surrounding areas provide an idyllic escape for every type of traveler.

  • Danbury: Located 14 miles from Pawling, Danbury is a vibrant city known for its stunning outdoor scenery and romantic spots. Visitors can experience a blend of shopping at the local mall and exploring educational venues. The city is home to attractive landmarks such as picturesque lakes and bustling tourist precincts, making it an ideal destination for those looking for a mix of relaxation and adventure. The event conference venues often host various activities and gatherings, adding to the city's charm.
  • Fishkill: Situated 15 miles from Pawling, Fishkill is a family-friendly city that offers an engaging urban experience. The area is perfect for outdoor enthusiasts and is equipped with excellent shopping centers and educational facilities. Notable attractions include a symbolic landmark and a thrilling theme park, perfect for family fun. Additionally, the visitor center provides resources and information to help travelers make the most of their stay in this lively community.
  • New Milford: Just 10 miles away from Pawling, New Milford is a picturesque city that captivates visitors with its charming outdoor settings and romantic ambiance. The city features a vibrant public market and various local markets, along with opportunities for skiing in the winter months. Nature lovers will be drawn to nearby lakes, the national state park, and serene beaches that provide a perfect backdrop for relaxation and exploration. New Milford is an ideal spot for those looking to immerse themselves in scenic beauty and outdoor activities.

Best time to go to Pawling

If you're planning a trip to Pawling, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January27.5°F (-2.5°C)Light RainMostly SunnyAverageSlightly Low
February29.3°F (-1.5°C)Light RainMostly CloudyAverageAverage
March36.7°F (2.6°C)Light RainMostly CloudyAverageSlightly Low
April48.0°F (8.9°C)Light RainMostly SunnySlightly HighSlightly Low
May58.8°F (14.9°C)Light RainMostly SunnyAverageAverage
June66.9°F (19.4°C)Light RainMostly SunnyAverageAverage
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighSlightly High
August71.4°F (21.9°C)Light RainMostly SunnyAverageSlightly High
September64.4°F (18.0°C)Light RainMostly SunnySlightly HighAverage
October53.6°F (12.0°C)Light RainMostly SunnySlightly LowAverage
November41.5°F (5.3°C)Light RainMostly SunnySlightly LowAverage
December33.6°F (0.9°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that meets your budget, utilize our handy filters to sort by price, location, and vacation rental type. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and enjoy the full benefits of OneKeyCash on your booking. Being the organizer really pays off. When you join our travel rewards program, One Key, you'll gain immediate access to member discounts and the opportunity to earn and redeem OneKeyCash on eligible reservations. Sign up today and start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a dedicated area for you to create new travel plans, manage your existing ones, and keep your bookings organized. The properties you've saved or reserved are neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Historic Pawling will entice you

Enjoy the history and other features of Pawling. This city has something for everyone. A vacation 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 discover things to do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Pawling has to offer. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Thunder Ridge Ski Resort (3.9 mi / 6.3 km)
  • Putnam County Golf Course (14.5 mi / 23.4 km)
  • Fishkill Golf Course (15.5 mi / 24.9 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)

Exploring the natural features in Pawling

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Pawling is a great spot to appreciate mother nature. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Emmanuel Williamson Park (8.3 mi / 13.4 km)
  • Candlewood Lake (9.2 mi / 14.7 km)
  • Bear Mountain Reservation (10.9 mi / 17.5 km)
  • Lake Mahopac (14.4 mi / 23.1 km)
  • Tarrywile Park and Mansion (14.8 mi / 23.9 km)
  • Rogers Park (14.9 mi / 23.9 km)

Traveling to and around Pawling

The nearest airport is in Danbury, CT (DXR-Danbury Municipal), located 14.4 mi (23.2 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Oxford, CT (OXC-Waterbury - Oxford), which is 24.7 mi (39.7 km) away.

If you'd rather travel by train, the main station serving the city is Appalachian Trail.

Frequently asked questions

What is the best area to stay in Pawling when booking a vacation rental?
When booking a vacation rental in Pawling, New York, the best area to consider is the charming downtown district. This area offers a delightful blend of convenience and local charm, making it an ideal spot for visitors. With a variety of vacation rental properties available, ranging from cozy cottages to more spacious homes, you'll find plenty of options to suit your needs.

Staying in downtown Pawling places you within walking distance of several popular attractions. One of the highlights is the historic Pawling Train Station, which is not only a beautiful architectural feature but also a gateway to the scenic Metro-North Railroad, connecting you to the bustling city of New York. The station is surrounded by quaint shops, cafes, and restaurants that reflect the town's vibrant community spirit.

Additionally, the nearby Pawling Nature Reserve is a fantastic destination for nature lovers. This expansive area offers serene walking trails, picturesque views, and opportunities for birdwatching, making it a superb spot for outdoor activities. The combination of these attractions, along with the welcoming atmosphere of downtown Pawling, ensures a memorable vacation experience.
How much does it cost to rent a vacation home in Pawling?
Prices for vacation 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 vacation 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.
Where are the best areas for renting a beach house in Pawling?
For renting a beach house in Pawling, New York, travelers should consider the picturesque spots along the shores of Lake Pawling. This area offers a selection of vacation homes with direct lake access, great for enjoying swimming, fishing, or kayaking. Many of these properties come equipped with amenities such as private docks, outdoor decks with seating, and spacious backyards ideal for summer gatherings.

Additionally, the nearby Dutchess County area has charming waterfront rentals that provide a serene lakefront experience. These accommodations often feature modern kitchens, cozy living areas, and some even include fire pits for evening relaxation by the water. Visitors can also enjoy local parks and nature trails, with many properties situated within close proximity to scenic hiking routes that offer beautiful views of the surrounding landscapes.

For those looking to explore the local culture, Pawling itself has quaint shops and dining options, enhancing the overall experience of a beach house rental.
What is the most popular type of vacation rental accomodation in Pawling?
In Pawling, vacation houses and cabins are the most popular types of rental accommodations, with several options available throughout the area. These rentals are typically situated in tranquil, scenic neighborhoods, providing a friendly space for relaxation. Most vacation houses come with multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups. Cabins offer a more rustic charm, often featuring cozy interiors, fireplaces, and outdoor spaces like decks or porches that allow guests to enjoy the natural beauty of the surrounding landscapes.
Are there any family house rentals in Pawling?
In Pawling, New York, there are several family-friendly house rentals available, making it a great spot for a family getaway. The local area features charming homes with spacious living areas, great for family gatherings. Many of these properties come equipped with full kitchens, allowing for enjoyable home-cooked meals, and outdoor spaces where children can safely play.

Visitors can explore the beauty of the nearby Appalachian Trail for hiking adventures or spend time at local parks, which often have playgrounds and picnic areas. Additionally, the quaint downtown area offers shops and eateries that cater to families.
Can I rent a vacation home with a pool or hot tub in Pawling?
In Pawling, New York, there are several vacation homes available for rent that feature pools and hot tubs, providing a great option for travelers looking to relax and enjoy the outdoors. This charming town offers a mix of scenic beauty and recreational opportunities, making it an appealing destination. Many of the rental properties come equipped with private pools, hot tubs, spacious patios, and outdoor seating areas, superb for gatherings or quiet evenings under the stars.

Travelers can also expect amenities such as fully equipped kitchens, comfortable living spaces, and proximity to local attractions, including hiking trails and nearby lakes.
Can I find long-stay vacation rentals in Pawling?
A long-stay vacation rental in Pawling is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Pawling?
In Pawling, visitors will find several pet-friendly house rentals that cater to both comfort and convenience. Many of these rentals come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can roam freely. The area is known for its charming rural ambiance and offers a variety of options, including cozy cottages and larger family homes.

Nearby, the Pawling Nature Reserve is an excellent destination for outdoor enthusiasts and pet owners alike, featuring walking trails and scenic views where pets are welcome. Additionally, the quaint downtown area of Pawling offers pet-friendly cafes and shops, fostering a welcoming environment for travelers with furry companions.
Are there any remote work vacation rentals in Pawling?
In Pawling, New York, there are several vacation rentals that cater specifically to remote workers. These properties often include essential amenities such as high-speed Wi-Fi, dedicated office spaces with desks and comfortable chairs, and quiet environments conducive to productivity. Many rentals provide additional comforts like fully equipped kitchens, cozy living areas, and outdoor spaces for breaks.

Pawling itself is a charming town with a picturesque downtown area, offering local shops and eateries. The scenic landscape, including nearby parks and trails, provides opportunities for outdoor activities during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pawling vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Pawling with parking available—perfect for families or travelers 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 vacation rental amenities include kitchens for preparing meals, WiFi for staying connected, and outdoor spaces like patios or decks for relaxation and enjoying the scenery. Many rentals also feature appliances such as blenders, making it convenient for guests to whip up smoothies or other meals during their stay.
When is the best time to visit Pawling for a vacation rental?
April marks the peak time to visit Pawling, New York, where travelers can take part in the beauty of spring. This vibrant period, spanning from March to May, attracts those seeking outdoor adventures, charming local events, and picturesque views of blossoming landscapes. As the weather warms up, visitors can enjoy hiking the scenic trails of the Appalachian Trail or exploring nearby parks, all while basking in the comfortable temperatures that typically range from the mid-40s to the low 70s Fahrenheit.

In April, you can look forward to a lively atmosphere as the community comes alive with various spring festivities. The town's quaint shops and eateries offer a delightful taste of local culture, making it an excellent time for relaxation and exploration.

If you're seeking a more budget-friendly option, consider visiting in December. This month, while quieter, offers its own unique charm with the festive holiday spirit in full swing. Winter walks through snow-dusted parks provide a serene escape, allowing you to appreciate the peaceful beauty of Pawling.

Ultimately, your choice of when to visit Pawling will depend on whether you prefer the vibrant energy of spring or the tranquil charm of winter.
How early should I book a Pawling vacation rental?
Book your Pawling vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Pawling?
In Pawling, New York, visitors can explore several charming attractions that highlight the area's natural beauty and historical significance. The Pawling Nature Reserve offers scenic trails for hiking and birdwatching, providing a peaceful retreat for nature lovers. The historic village center features quaint shops and eateries, where travelers can enjoy local cuisine and unique finds.

Nearby, the Appalachian Trail crosses the area, making it a popular spot for hiking enthusiasts seeking beautiful vistas and outdoor activities. Additionally, the Dutchess Golf Club provides opportunities for golf enthusiasts to enjoy a round while taking in picturesque views of the surrounding landscape.
Can I change or cancel my Pawling home rental booking on Vrbo?
To find Pawling vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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