Best Vacation Homes in Bennington County
1650 ft²
8 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $279/Night
For 7 Nights US $1,953
1550 ft²
7 Guests
1 Bedroom
3 Bathrooms
Free Cancellation
House
- Skiing
- Fireplace/Heating
- Air Conditioner
US $793/Night
For 7 Nights US $5,549
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $182/Night
For 7 Nights US $1,271
2500 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $566/Night
For 7 Nights US $3,963
1001.04 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Skiing
- Fireplace/Heating
- Pool
US $449/Night
For 7 Nights US $3,145
1300 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $504/Night
For 7 Nights US $3,528
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $184/Night
For 7 Nights US $1,285
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $271/Night
For 7 Nights US $1,898
Bennington County Luxury Rentals
15000 ft²
26 Guests
15 Bedrooms
13 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $4,589/Night
For 7 Nights US $32,124
4300 ft²
16 Guests
9 Bedrooms
6 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $4,080/Night
For 7 Nights US $28,561
24 Guests
9 Bedrooms
6 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Internet
US $3,456/Night
For 7 Nights US $24,192
6500 ft²
24 Guests
9 Bedrooms
7 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Skiing
US $3,280/Night
For 7 Nights US $22,960
9000 ft²
26 Guests
11 Bedrooms
8 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Spa
US $2,707/Night
For 7 Nights US $18,949
9000 ft²
34 Guests
15 Bedrooms
10 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $2,660/Night
For 7 Nights US $18,622
8 Guests
4 Bedrooms
3 Bathrooms
Group Friendly
Ski Chalet
- Private Pool
- Fireplace/Heating
- Pool
US $1,973/Night
For 7 Nights US $13,814
22 Guests
8 Bedrooms
10 Bathrooms
Pet Friendly
House
- Skiing
- Fireplace/Heating
- Breakfast
US $1,947/Night
For 7 Nights US $13,627
Bennington County Pet Friendly Vacation Rentals
768 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $335/Night
For 7 Nights US $2,347
2798.62 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $755/Night
For 7 Nights US $5,283
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Pet Friendly
US $679/Night
For 7 Nights US $4,753
900 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $301/Night
For 7 Nights US $2,107
2497.23 ft²
5 Guests
2 Bedrooms
2 Bathrooms
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $478/Night
For 7 Nights US $3,349
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $220/Night
For 7 Nights US $1,542
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $361/Night
For 7 Nights US $2,524
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $271/Night
For 7 Nights US $1,896
Bennington County Large Vacation Homes
4000 ft²
11 Guests
6 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $659/Night
For 7 Nights US $4,616
6146.19 ft²
15 Guests
1 Bedroom
4 Bathrooms
Ocean View
House
- Private Beach
- Spa
- Skiing
US $1,467/Night
For 7 Nights US $10,266
5400 ft²
12 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $1,236/Night
For 7 Nights US $8,655
241.59 ft²
44 Guests
18 Bedrooms
18 Bathrooms
Ocean View
Bed & Breakfast
- Oceanfront
- Skiing
- Fireplace/Heating
US $185/Night
For 7 Nights US $1,295
4100 ft²
11 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $619/Night
For 7 Nights US $4,332
2600 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $406/Night
For 7 Nights US $2,844
4000 ft²
14 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $657/Night
For 7 Nights US $4,601
11 Guests
7 Bedrooms
4 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $667/Night
For 7 Nights US $4,667
Why Choose Rent By Owner for your Bennington County 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 Bennington County
When should you plan your Vacation Rentals stay?
To make the most of your visit, consider planning your getaway during the optimal seasons when the area offers ideal weather and activities, ensuring a memorable experience in this charming region.
Peak Season Highlights
Summer (June to August)
During summer, this area experiences warm weather, making it ideal for outdoor activities and exploring the scenic landscapes. Booking your vacation rentals now ensures you enjoy the full beauty of the region when nature is at its most vibrant.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn transforms the landscape with stunning fall foliage, attracting visitors seeking picturesque scenery. Reserve your vacation rentals early to experience the region’s breathtaking colors during this popular season.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
In winter, the area offers a peaceful retreat with opportunities for winter sports and cozy getaways. Booking your vacation rentals during this time allows you to enjoy more tranquility and better rates.
Average Temperature Daytime: 20°F to 35°F - Nighttime: 5°F to 15°F
Spring (March to May)
As the region awakens from winter, spring brings mild weather and blooming landscapes. Securing your vacation rentals ahead of the busy season ensures a comfortable stay while experiencing the area's natural renewal.
Average Temperature Daytime: 45°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Bennington County
How to Book Your Bennington County 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.
Explore and book the perfect rental in Bennington County
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 outdoor dining options with picnic tables or BBQ grills available on the property.
- Relax outside on a private patio, porch, or deck with scenic views of the surrounding landscape.
- Take advantage of outdoor recreational facilities such as tennis courts, basketball hoops, or playgrounds.
- Explore the natural beauty nearby with access to hiking trails or walking paths directly from your rental.
- If available, unwind in a hot tub or spa set amidst the fresh air and tranquil scenery.
- Make use of outdoor fire pits for cozy evenings under the stars with friends or family.
- Benefit from ample outdoor parking space to conveniently accommodate your vehicle during your stay here.
Top Attractions Around Bennington County
What attractions are nearby?
Here, you can explore a variety of outdoor activities and charming local attractions that make this destination an ideal spot for a memorable getaway.
Family Activities
- Bennington Museum: Explore engaging exhibits and art collections that captivate children and adults alike, making it a delightful stop for families in the region.
- Hildene, The Lincoln Family Home: Discover historic estate tours and scenic gardens where the entire family can enjoy learning about history and nature in this part of Vermont.
- Grafton Ponds Outdoor Center: Experience outdoor activities such as pond skating, snowshoeing, and cross-country skiing that cater to families seeking winter adventure in the area.
- Northshire Bookstore: Spend time browsing a beloved local bookstore offering storytime events and cozy spaces perfect for family reading sessions in the destination's charming downtown.
Adult Activities
- Hiking and Scenic Trails: Explore the region’s picturesque landscapes by hiking along its well-maintained trails, immersing yourself in the natural beauty that defines this destination.
- Historic Museums and Cultural Sites: Discover the area's rich history and vibrant arts scene through visits to local museums and cultural landmarks.
- Farmers Markets and Local Cuisine: Savor fresh, regional flavors at farmers markets and enjoy authentic Vermont cuisine that showcases the area's agricultural heritage.
- Outdoor Recreation and Sports: Engage in outdoor activities such as kayaking, fishing, or cycling, taking advantage of the region's diverse outdoor recreation opportunities.
Other Places to Stay in Bennington County, VT
Bennington
Manchester
Bondville
Manchester Center
Londonderry
Sunderland
Arlington
Dorset
Bromley Mountain
Bromley Mountain Ski Resort
Winhall
Bennington County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Seasonal Attractions: Research the area's seasonal highlights to time your visit and explore activities that showcase the best of the region during your stay.
- Choose the Perfect Location: Select a vacation rental in a central or scenic part of the destination to enjoy easy access to local sights and immerse yourself in the area's natural beauty.
- Explore Local Dining Options: Take advantage of the local culinary scene by trying nearby eateries, which offer authentic flavors and a taste of the region’s culture.
- Utilize Public and Outdoor Transportation: Make the most of available transportation options around here to explore without hassle and maximize your experience in this charming destination.
Transportation Options
- Bennington County Transit System: Offers reliable local bus services that make exploring this region convenient without needing a personal vehicle.
- Amtrak Vermont Rail Service: Provides scenic train travel connecting the area to major cities, ideal for visitors seeking a relaxed journey into this charming destination.
- Rental Car Services: Numerous car rental companies operate in the region, giving you the flexibility to explore the area's attractions at your own pace.
- Taxi and Ride-Sharing Services: Convenient transportation options available throughout here, perfect for quick trips or last-minute travel needs within the area.
Local Customs Options
- Bennington County's Maple Sugar Season: Participating in the local maple sugaring tradition during the spring offers an authentic taste of the area's enduring agricultural heritage.
- Vermont's Native Craftsmanship: Appreciating handcrafted goods, from pottery to woodworking, reflects the region’s deep-rooted artisanal customs you can explore nearby.
- The Local Harvest Festivals: Engaging in seasonal festivals celebrates the area's bountiful produce and farming traditions throughout the region.
- Historic Preservation Practices: Respecting local historical sites and participating in community-led conservation efforts highlights the area's commitment to maintaining its heritage for visitors like you.
Bennington County Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Bennington County?
There are a lot of options in Bennington County. If you plan on staying in the Bennington County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Bennington County:
- The Inn at Manchester
- Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
- Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
- Charming Vermont Home on 7 Acres w/Hot Tub, Pond, Bonfire Pit & 3 Fireplaces!
- Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
- Private secluded trout cabin- sleeps 2
- Historic 1820s Homestead on Battenkill River!
- Luxury home in the heart of Manchester. Walk to shops; minutes to mountains.
- Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
- MANCHESTER HOME - BREATHTAKING VIEWS! LOCATION! GOLF! SKIING! SHOPPING! HOT TUB!
2. How many vacation rentals have private pools in Bennington County?
There are 25 vacation rentals with private pools near Bennington County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Bennington County are best for families?
If you are looking for a family-friendly vacation home in Bennington County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Bennington County:
4. How many Rentbyowner vacation rentals are available in Bennington County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 955 in the Bennington County 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 Bennington County.
5. What is the cancellation policy for vacation rentals in Bennington County, Vermont?
Cancellation policies vary by property. It’s important to review the specific listing details or contact the property owner directly to understand the terms and any potential fees related to cancellations in this area.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or local taxes may apply. These details are typically listed on the property page, so be sure to read the full description or reach out to the host for clarification.
7. How do I ensure my reservation is secure when booking a vacation rental in this destination?
Booking through a trusted platform offers secure payment options and verified host profiles. Always confirm the listing’s reviews and communicate directly with the property owner if you have any concerns before finalizing your booking.
8. What amenities can I expect from vacation rentals in the region?
Most properties offer essential amenities like Wi-Fi, fully equipped kitchens, and parking. For specific features, review each listing carefully or contact the host directly to ensure it meets your travel needs.
9. Is it possible to make special requests or arrangements for my stay in this area?
Many hosts are willing to accommodate special requests, such as late check-ins or additional amenities. Contact the property owner prior to booking to discuss any specific requirements you might have for your visit.
Bennington County Top Rated Vacation Rentals
1391 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $363/Night
For 7 Nights US $2,540
750 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Skiing
- Fireplace/Heating
- Pool
US $205/Night
For 7 Nights US $1,437
1818 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $513/Night
For 7 Nights US $3,589
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $525/Night
For 7 Nights US $3,675
2700 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $288/Night
For 7 Nights US $2,017
5000 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Pool
US $1,473/Night
For 7 Nights US $10,312
US $291/Night
For 7 Nights US $2,037
1800 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Skiing
- Fireplace/Heating
- Pool
US $432/Night
For 7 Nights US $3,024
