Discover Your Perfect Old Bennington Vacation Homes

Old Bennington Luxury Rentals

9.6 (10 Reviews)
Apartment
Green Mountain Getaway
  • Air Conditioner
  • Parking
  • Security/Safety
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Why Choose Rent By Owner for your Old 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.

Best Times to Visit Old Bennington

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience, so consider planning your getaway during the season that best aligns with your interests in this charming destination.

Peak Season Highlights

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Summer (June to August)

During the summer months, you can enjoy warm weather and longer daylight hours, making it ideal for exploring the area's scenic beauty and outdoor activities.

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

The fall season offers vibrant foliage and pleasant temperatures, perfect for experiencing the region's natural colors and local events.

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)

In winter, the area transforms into a snowy wonderland, providing cozy settings for relaxation and winter sports enthusiasts seeking quiet escapes.

Average Temperature Daytime: 20°F to 35°F - Nighttime: 5°F to 15°F
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Spring (March to May)

Spring brings milder weather and blooming landscapes, though shoulder seasons tend to be quieter, offering more tranquility when booking your stay.

Average Temperature Daytime: 45°F to 60°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Old Bennington

How to Book Your Old 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 Old Bennington

More Top-Rated Vacation Rentals in Old 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 a spacious outdoor patio or deck perfect for relaxing or al fresco dining amidst the scenic surroundings.
  • Take advantage of well-maintained gardens or landscaped yards to enhance your outdoor experience.
  • Make use of outdoor grills or barbecue facilities to prepare traditional Vermont cuisine with ease.
  • Benefit from private or shared outdoor seating areas ideal for socializing and enjoying the fresh air.
  • Utilize dedicated parking spaces in a convenient outdoor setting close to your rental home.
  • Embrace the region’s natural beauty with access to walking trails or pathways directly from your accommodation.
  • Relish in seasonal outdoor amenities such as fire pits or hammocks, perfect for unwinding after exploring here.

Top Attractions Around Old Bennington

What attractions are nearby?

Enjoy a variety of outdoor activities and local attractions just moments from your vacation rental in Old Bennington, offering an authentic experience of the area's natural beauty and charming heritage.

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Family Activities

  • Bennington Battle Monument: Explore this historic landmark to learn about the area's pivotal role in American history and enjoy panoramic views from the observation deck.
  • Bennington Museum: Discover art, regional history, and exhibits that captivate visitors of all ages right in the heart of this charming destination.
  • Hiking at Mount Anthony Union Park: Embark on family-friendly trails offering scenic vistas and outdoor fun amid the natural beauty surrounding here.
  • Bennington Center for the Arts: Experience engaging art classes, exhibitions, and performances designed to inspire creativity and family bonding in the region.
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Adult Activities

  • Bennington Museum Tour: Explore the region’s rich history and art collections at this renowned museum, perfect for immersing yourself in local culture.
  • Driving Historic Scenic Routes: Embark on a scenic drive through the area to enjoy picturesque landscapes and learn about the region's historical significance.
  • Local Art Galleries Visit: Discover vibrant art galleries showcasing works inspired by Vermont's natural beauty, ideal for leisurely afternoons.
  • Dining at Farm-to-Table Restaurants: Savor locally sourced cuisine in the area's acclaimed restaurants that emphasize regional flavors and culinary craftsmanship.

Other Places to Stay in Old Bennington, VT

Old First Congregational Church
Old First Congregational Church Vacation Rentals
Bennington Museum
Bennington Museum Vacation Rentals
Bennington Battle Monument
Bennington Battle Monument Vacation Rentals
More Places to Stay Near Old Bennington

Old Bennington Travel Tips

How Can You Make the Most of Your Stay?

  • Explore historic sites: Immerse yourself in the area's rich history by visiting notable landmarks, enhancing your understanding and appreciation of the region's heritage.
  • Enjoy local cuisine: Savor authentic flavors at nearby eateries to get a true taste of the regional culinary traditions during your stay.
  • Plan outdoor activities: Take advantage of the scenic landscape by exploring outdoor pursuits such as hiking or cycling, which showcase the natural beauty of this destination.
  • Connect with local events: Check out community events and festivals happening during your visit to experience the vibrant culture of the area firsthand.

Transportation Options

  • Bennington Airport Shuttle Service: This convenient service offers reliable transportation between the area and nearby airports, making your arrival and departure smooth and stress-free.
  • Rental Cars: Several local providers in the region enable you to explore at your own pace, giving you flexibility during your stay here.
  • Taxis and Rideshare Services: Easily accessible within this destination, these options provide quick transport for short trips around town or to neighboring attractions.
  • Public Bus System: The regional transit system connects various parts of the area, offering an economical way to navigate around here without the need for personal vehicle rental.

Local Customs Options

  • Bennington Battle Day Traditions: Locals and visitors alike observe this regional holiday with parades and ceremonies that honor the area's historical significance.
  • Vermont Maple Syrup Customs: You’ll find that sharing and sampling this regional specialty is an integral part of experiencing here’s local hospitality and culinary heritage.
  • Farmers' Market Etiquette: Engaging respectfully with vendors and supporting local artisans reflects the community's appreciation for its agricultural roots.
  • Historic Preservation Practices: Respect for the region’s historic sites and architecture plays a key role in maintaining the area's charming atmosphere for residents and visitors alike.

Frequently Asked Questions About Old Bennington?

1. What are the top vacation rentals in Old Bennington?

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

2. Which vacation homes in Old Bennington are best for families?

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

3. How many Rentbyowner vacation rentals are available in Old Bennington?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 59 in the Old 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 Old Bennington. 

4. What is the cancellation policy for vacation rentals in this area?

The cancellation policy varies by property. You should review the specific listing details or contact the host directly to understand the terms and any applicable fees before confirming your reservation.

5. How do I know if a vacation rental in Bennington offers flexible booking options?

Flexible booking options are specified in each listing. Check the property details or reach out to the owner to confirm if they allow modifications or cancellations without penalties.

6. Are there any specific requirements or house rules I should be aware of when booking here?

Each vacation rental has its own set of house rules, which are detailed within the listing. It’s advisable to read these carefully and communicate with the owner if you have any questions.

7. What amenities are typically included in vacation rentals near Bennington?

Most rentals in this region offer amenities such as Wi-Fi, parking, and kitchen facilities. For exact amenities available, please refer to the individual listing details.

8. How can I ensure my stay aligns with the local regulations and safety standards?

All vacation rentals in the area are required to comply with local safety standards. Confirm with the property owner that the rental meets all health and safety requirements before finalizing your booking.