Best Vacation Homes in Pawling
Cottage
10.0(9 Reviews)
2 Bedrooms
1 Bath
7 Guests
Parking
Ocean View
Balcony/Terrace
View
US $530/Night
7 Nights - US $3,708
House
2 Bedrooms
1 Bath
4 Guests
1496.18 ft²
- Parking
Pool- Balcony/Terrace
Internet
US $813/Night
7 Nights - US $5,689
House
9.2(205 Reviews)
1 Bedroom
1 Bath
- Parking
Kitchen
Air Conditioner- Internet
US $168/Night
7 Nights - US $1,178
House
10.0(1 Review)
5 Bedrooms
2 Baths
10 Guests
2000 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $790/Night
7 Nights - US $5,529
Other
1 Bedroom
1 Bath
5 Guests
495.14 ft²
- Parking
Pet Friendly
Child Friendly
US $175/Night
7 Nights - US $1,225
House
9.0(10 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
Spa- Ocean View
US $507/Night
7 Nights - US $3,552
House
10.0(133 Reviews)
3 Bedrooms
2 Baths
6 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $595/Night
7 Nights - US $4,165
House
10.0(72 Reviews)
3 Bedrooms
3 Baths
6 Guests
2750 ft²
Hot Tub- Parking
- Ocean View
- Balcony/Terrace
US $615/Night
7 Nights - US $4,305
Pawling Luxury Rentals
House
10.0(20 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $925/Night
7 Nights - US $6,474
House
9.8(20 Reviews)
4 Bedrooms
4 Baths
8 Guests
Oceanfront- Parking
Skiing- Ocean View
US $863/Night
7 Nights - US $6,038
Villa
2 Bedrooms
1 Bath
4 Guests
- Pool
- Air Conditioner
- Internet
- Child Friendly
US $765/Night
7 Nights - US $5,352
House
10.0(2 Reviews)
2 Bedrooms
3 Baths
6 Guests
2500 ft²
Private Pool- Parking
- Pool
- Balcony/Terrace
US $716/Night
7 Nights - US $5,012
Cabin
9.8(19 Reviews)
4 Bedrooms
3 Baths
8 Guests
2500 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $696/Night
7 Nights - US $4,870
House
9.6(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
2200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $632/Night
7 Nights - US $4,424
House
3 Bedrooms
3 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $463/Night
7 Nights - US $3,239
Cottage
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $377/Night
7 Nights - US $2,637
Pawling Pet Friendly Vacation Rentals
House
2 Bedrooms
2 Baths
6 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $311/Night
7 Nights - US $2,180
Apartment
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $124/Night
7 Nights - US $870
Cabin
10.0(70 Reviews)
4 Bedrooms
3 Baths
6 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $787/Night
7 Nights - US $5,511
House
10.0(58 Reviews)
3 Bedrooms
1 Bath
6 Guests
1056 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $249/Night
7 Nights - US $1,740
Cabin
10.0(4 Reviews)
5 Bedrooms
3 Baths
12 Guests
3800 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,029/Night
7 Nights - US $7,206
Cabin
10.0(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $634/Night
7 Nights - US $4,437
Cabin
9.4(13 Reviews)
1 Bedroom
1 Bath
6 Guests
864 ft²
Breakfast- Parking
- Spa
- Balcony/Terrace
US $229/Night
7 Nights - US $1,601
House
8.6(4 Reviews)
6 Bedrooms
4 Baths
12 Guests
3000 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $460/Night
7 Nights - US $3,220
Pawling Large Vacation Homes
House
5 Bedrooms
2 Baths
8 Guests
- Child Friendly
US $925/Night
7 Nights - US $6,475
House
10.0(6 Reviews)
6 Bedrooms
3 Baths
12 Guests
4000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $723/Night
7 Nights - US $5,063
House
10.0(5 Reviews)
4 Bedrooms
4 Baths
10 Guests
3200 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $914/Night
7 Nights - US $6,398
House
10.0(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $943/Night
7 Nights - US $6,598
House
10.0(1 Review)
6 Bedrooms
3 Baths
10 Guests
5000 ft²
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $550/Night
7 Nights - US $3,850
House
9.6(14 Reviews)
6 Bedrooms
5 Baths
16 Guests
5500 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $758/Night
7 Nights - US $5,306
House
4 Bedrooms
3 Baths
10 Guests
3361 ft²
- Hot Tub
- Air Conditioner
- Internet
- Pet Friendly
US $500/Night
7 Nights - US $3,500
Why Choose Rent By Owner for your Pawling Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Pawling
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit here can enhance your experience, as this destination offers different charms depending on the season, making it essential to plan your trip when the region’s natural beauty and local events align with your preferences.
Peak Season Highlights
Summer (June to August)
This is the most popular time to visit the area, as the warm weather and extended daylight hours make outdoor activities enjoyable. You can experience the region at its lively best, making it ideal for those seeking vibrant local events and scenic outdoor adventures.
Average Temperature Daytime: around 80°F - Nighttime: around 60°F
Autumn (September to November)
During these months, the region transforms with stunning fall foliage, attracting visitors who want to enjoy scenic drives and outdoor excursions amidst colorful landscapes. It’s an excellent period for relaxing stays in cozy vacation rentals while experiencing the area's natural beauty.
Average Temperature Daytime: around 65°F - Nighttime: around 45°F
Off-Season Highlights
Winter (December to February)
The quiet winter months offer a peaceful escape with fewer visitors in the area. If you enjoy crisp air and scenic winter landscapes from your lodging, this season provides a serene environment for your stay in vacation rentals.
Average Temperature Daytime: around 35°F - Nighttime: around 20°F
Spring (March to May)
As the region awakens from winter dormancy, spring presents an ideal time for those seeking fewer crowds and blooming scenery. Vacation rentals become adorable retreats, perfect for enjoying the early signs of new life in the area.
Average Temperature Daytime: around 55°F - Nighttime: around 35°F
Weekly Weather Forecast for Pawling
How to Book Your Pawling Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a spacious outdoor patio or deck for relaxing and entertaining in the fresh air.
- Take advantage of a well-maintained private garden or yard to connect with nature during your stay.
- Experience outdoor dining options with a grill or barbecue area perfect for warm-weather meals.
- Make the most of nearby hiking or walking trails that showcase the scenic beauty of the region.
- Leverage access to a fire pit or outdoor fireplace for cozy evenings under the stars.
- Benefit from ample parking spaces, often complemented by easy access to outdoor amenities.
- Utilize outdoor recreational features like a swimming pool or tennis court available at select properties here.
Top Attractions Around Pawling
What attractions are nearby?
Within proximity to your stay, you can enjoy outdoor activities such as hiking, fishing, and exploring scenic nature trails that showcase the natural beauty of this destination.
Family Activities
- Exploring the Pawling Nature Preserve: Enjoy family-friendly hiking and wildlife viewing in this scenic preserve, providing a perfect outdoor adventure here.
- Pawling Central Park: Spend quality time picnicking, playing, or strolling through this local park, which offers a relaxing spot for families to unwind in the area.
- Pawling Public Library: Engage with interactive programs and storytime sessions suitable for children, making it an educational highlight of your stay.
- Visit to the Dutcher Memorial Park & Playground: Let the kids enjoy the playground and open space while you relax nearby, all within close proximity to the region's vacation rentals.
Adult Activities
- Hiking at the Appalachian Trail: Experience breathtaking views and peaceful nature walks along one of the region's most renowned trails.
- Golf at the Quaker Hill Golf Course: Enjoy a round of golf amidst the scenic landscapes characteristic of this destination’s lush courses.
- Visit the Harlem Valley Rail Trail: Explore the area on a leisurely bike ride or walk along this scenic trail that showcases the region’s natural beauty.
- Enjoy local wines at nearby vineyards: Savor tastings and explore the wine-making traditions in the vicinity for a relaxed adult activity.
Other Places to Stay in Pawling, NY
John Kane House
Pawling Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead: Explore local events and seasonal activities to tailor your stay for an authentic experience in this charming area.
- Choose a Prime Location: Select a vacation rental near key attractions or natural spots to maximize your time and convenience here.
- Explore Local Cuisine: Take advantage of nearby eateries and farm-to-table options to enjoy the region’s culinary offerings during your visit.
- Engage with Nature: Incorporate outdoor adventures like hiking or walking to truly immerse yourself in the scenic beauty of here.
Transportation Options
- Car Rentals: Renting a vehicle is a convenient way to explore the scenic region surrounding Pawling, offering flexibility and comfort during your stay.
- Public Transit: The local bus services provide an affordable and reliable transportation option for getting around this area and connecting to nearby destinations.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing apps are readily available, providing quick and direct transportation options within the region.
- Regional Trains: Amtrak serves nearby cities and offers a comfortable travel alternative for those looking to explore beyond Pawling's charming surroundings.
Local Customs Options
- Local Farming Traditions: You can experience the region’s rich agricultural heritage through community farmers' markets and farm-to-table dining experiences that celebrate local produce.
- Historical Preservation Practices: Respect for the area's history is evident in its well-maintained historic sites and architecture, offering a glimpse into its past for visitors staying in nearby vacation rentals.
- Seasonal Festivals: Participating in seasonal events and festivals allows you to immerse yourself in the community’s vibrant culture and customs here during your stay.
- Community Art Initiatives: The region supports local artists and artisans, with frequent galleries and craft markets showcasing handmade works, perfect for exploring during your visit.
Pawling Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Pawling?
There are a lot of options in Pawling. If you plan on staying in the Pawling area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pawling:
- Quiet Lakefront Retreat only 80 minutes from NYC- with Private Dock
- Peaceful & Quiet Lakeside Home with Hot Tub, Pool Table, Fire Pit
- Beautiful lake view home on Whaley Lake in Holmes, NY.
- Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
- Harlem Valley Hideout - Artsy Home with Pool & Tennis
- Perfection in Litchfield County
- Beautiful Lake View House Overlooking Peaceful Whaley Lake
- Woodstove, firepit, lakeviews and access to lake, hiking trails, large terrace!
- "Country outside the city " 3 bedrooms 2 full bathrooms
- Station Inn Pawling
2. Which vacation homes in Pawling are best for families?
If you are looking for a family-friendly vacation home in Pawling, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pawling:
3. How many Rentbyowner vacation rentals are available in Pawling?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 51 in the Pawling area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Pawling.
4. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property; you should review the specific listing details or contact the owner directly to understand the terms and any applicable fees for cancellations.
5. How do I confirm my booking at a vacation rental here?
Once you select your preferred property, you will need to follow the booking process outlined on the listing, which often involves submitting payment and receiving confirmation from the owner or property manager.
6. Are pets allowed in vacation rentals in this region?
Pet policies differ between properties; check the individual listing for pet allowances and any additional fees or restrictions before completing your reservation.
7. What amenities are typically included in the vacation rentals in this destination?
Amenities vary by property, but common features include Wi-Fi, parking, and fully equipped kitchens. You should review each listing's amenities section for detailed information.
8. Is there a minimum stay requirement for booking a vacation rental here?
Minimum stay requirements are set by individual owners and can vary; refer to the specific property listing or contact the owner for details.
Pawling Top Rated Vacation Rentals
Cottage
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
1500 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $774/Night
7 Nights - US $5,421
Other
10.0(1 Review)
3 Bedrooms
1 Bath
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $307/Night
7 Nights - US $2,148
House
3 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $587/Night
7 Nights - US $4,110
