Discover Your Perfect Bennington Vacation Homes

Best Vacation Homes in Bennington

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10.0 (245 Reviews)
Bed & Breakfast
The Inn at Manchester
  • Air Conditioner
  • Parking
  • Pool
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10.0 (1 Review)
House
Sunderland Guest House
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
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Bennington Luxury Rentals

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Bennington Pet Friendly Vacation Rentals

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Bennington Large Vacation Homes

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9.8 (44 Reviews)
Bed & Breakfast
The Dorset Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
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Why Choose Rent By Owner for your Bennington Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Bennington Vacation Rentals

Where are the best neighborhoods to stay in Bennington?

When planning your stay in Bennington, Vermont, exploring the different neighborhoods can help you find the perfect spot to experience the charm and tranquility of this historic area. Whether you prefer a lively downtown setting or a peaceful retreat surrounded by natural beauty, each neighborhood offers unique attractions and amenities suited to your preferences. By selecting the right location within Bennington, you'll enjoy convenient access to local attractions and the serene atmosphere that makes this Vermont town so special. Booking your vacation rental in one of these neighborhoods ensures a comfortable and memorable visit to Bennington.

Forest Farms

Nestled within the scenic surroundings of Vermont, Forest Farms offers a peaceful retreat where you can enjoy nature’s tranquility. Its proximity to lush landscapes makes it an ideal spot for those seeking a serene getaway in this region.

View 455+ Rentals in Forest Farms

Bromley Mountain

Located near the popular Bromley Mountain, this area provides convenient access to outdoor adventures and winter sports, making it perfect for active travelers exploring Vermont’s mountain charm.

View 32+ Rentals in Bromley Mountain

Best Times to Visit Bennington

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, as the region offers unique outdoor and cultural activities across different seasons, making it ideal for planning your perfect getaway at your preferred time of year.

Peak Season Highlights

summer
Summer (June to August)

During the peak summer months, the region experiences warm weather, making it ideal for outdoor activities and exploring the local scenery. Booking your vacation rentals now ensures you enjoy the best of this vibrant season.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to October)

As autumn arrives, the area's landscapes transform with colorful foliage, attracting visitors seeking picturesque views and outdoor adventures. Securing your accommodations early can enhance your experience here during this scenic season.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Winter (December to February)

The colder months bring a quieter atmosphere, perfect for those who prefer a peaceful retreat or winter sports. Booking your vacation rentals in advance guarantees cozy accommodations before the busy season begins.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
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Spring (March to May)

In early spring, the area starts to awaken with blooming flora and milder weather, offering a tranquil escape before the high season. Planning ahead helps secure your ideal rental during this transitional period.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Bennington

How to Book Your Bennington 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

More Top-Rated Vacation Rentals in Bennington Area

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 grilling stations to prepare meals amidst the scenic surroundings.
  • Relax in private patios or decks with comfortable seating to take in the fresh mountain air.
  • Take advantage of spacious yards perfect for outdoor activities and family games.
  • Make use of fire pits for cozy evenings under the stars after exploring the region.
  • Access nearby hiking trails and walking paths directly from your rental property.
  • Benefit from outdoor swimming pools or hot tubs available at select properties.
  • Utilize ample parking spaces designed to accommodate visitors exploring the area’s attractions.

Top Attractions Around Bennington

What attractions are nearby?

From exploring scenic hiking trails to discovering local galleries, there are plenty of outdoor and cultural activities nearby that allow you to fully enjoy the charm of this destination in Vermont's beautiful region.

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Family Activities

  • Bennington Battle Monument: You can explore this historic landmark that offers panoramic views and a glimpse into the area's rich history.
  • Nature Walks in Mount Anthony Park: Enjoy family-friendly trails and outdoor picnics surrounded by scenic landscapes unique to this part of Vermont.
  • Bennington Museum: Discover local art, unique exhibits, and cultural heritage that provide engaging experiences for children and adults alike.
  • Old First Church: Visit this charming historic site where you can take part in family-friendly tours and community events held here throughout the year.
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Adult Activities

  • Bennington Museum: Explore a rich collection of American art and regional history, offering insight into the area's cultural heritage.
  • The Bennington Battle Monument: Visit this iconic landmark to learn about an important Revolutionary War victory while enjoying panoramic views from the top.
  • The Vermont Summer Festival Horse Show: Attend this renowned equestrian event that attracts enthusiasts and competitors from across the country.
  • Hiking in Mount Anthony Union Park: Discover scenic trails and breathtaking vistas, perfect for outdoor recreation and relaxing amidst nature.

Other Places to Stay in Bennington, VT

Manchester
Manchester Vacation Rentals
Peru
Peru Vacation Rentals
Manchester Center
Manchester Center Vacation Rentals
Sandgate
Sandgate Vacation Rentals
Sunderland
Sunderland Vacation Rentals
Shaftsbury
Shaftsbury Vacation Rentals
Arlington
Arlington Vacation Rentals
Woodford
Woodford Vacation Rentals
Winhall
Winhall Vacation Rentals
Dorset
Dorset Vacation Rentals
East Dorset
East Dorset Vacation Rentals
Bondville
Bondville Vacation Rentals
More Places to Stay Near Bennington

Bennington Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local culinary delights: Take the time to visit nearby eateries and farms to experience authentic regional flavors that complement your stay here.
  • Plan outdoor activities: Make the most of the area's natural beauty by scheduling hiking, biking, or scenic drives to discover hidden gems in this destination.
  • Visit cultural landmarks: Incorporate visits to notable historic sites and museums in the region to enrich your understanding of its unique heritage.
  • Book accommodations early: Secure your preferred vacation rentals well in advance to ensure a comfortable and convenient stay during peak seasons in this area.

Transportation Options

  • Bennington Transit System: This local bus service offers convenient transportation across the area, making it easy for you to explore the region without a car.
  • Rental Cars: Numerous rental agencies in the vicinity provide flexible options for exploring the scenic destinations around this Vermont locale at your own pace.
  • Taxi Services: Trusted taxi providers are available to offer quick and reliable rides within and around the region, ensuring seamless travel between your vacation rentals and nearby attractions.
  • Amtrak Train Service: The nearby train station connects this destination with major cities, offering a comfortable and scenic way to arrive or depart from your stay here.

Local Customs Options

  • Bennington’s Fall Foliage Traditions: During autumn, the region celebrates the vibrant change of leaves with community events that highlight Vermont's renowned fall colors.
  • Local Artisan Craftsmanship: The area values handcrafted goods, and you'll find many local artisans showcasing traditional Vermont craft techniques in markets and shops.
  • Historical Museum Visits: Preserving its rich history, here you can engage with local museums that honor Bennington’s past through exhibits and guided tours.
  • Seasonal Agricultural Festivals: The community hosts lively festivals centered around harvest time, emphasizing Vermont’s agricultural heritage and seasonal produce.

Frequently Asked Questions About Bennington?

1. What are the top vacation rentals in Bennington?

There are a lot of options in Bennington. If you plan on staying in the Bennington 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:

2. How many vacation rentals have private pools in Bennington?

There are 17 vacation rentals with private pools near Bennington. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Bennington are best for families?

If you are looking for a family-friendly vacation home in Bennington, 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:

4. How many Rentbyowner vacation rentals are available in Bennington?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 618 in the Bennington 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. 

5. What is the cancellation policy for vacation rentals in Bennington, Vermont?

Cancellation policies vary by listing, so it's important to review the specific terms on each property’s page. You can find detailed information about refunds and cancellation deadlines there or contact the owner directly for clarification.

6. Are there any additional fees associated with booking a vacation rental in this area?

Additional fees such as cleaning, service charges, or taxes may apply depending on the property. These details are typically outlined during the booking process or in the listing description, so be sure to review them before confirming your reservation.

7. What amenities are typically available in vacation rentals around this destination?

Amenities can differ from one property to another, but common offerings include kitchen facilities, Wi-Fi, parking, and outdoor spaces. To ensure the property meets your needs, check the amenities listed on each rental’s page before booking.

8. How do I confirm the availability of a vacation rental in the region?

Availability calendars are usually kept up-to-date on each listing. You can select your desired dates and see real-time availability, or reach out to the host directly for confirmation if needed.

9. What should I do if I encounter issues during my stay in a vacation rental here?

If you experience any problems, contact the property owner or manager as soon as possible. For unresolved issues, you may also reach out to the platform’s customer support for assistance to ensure a smooth stay.

Bennington Top Rated Vacation Rentals

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