Holiday Rentals in Bennington, VT

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Bennington, VT holiday rentals
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48 Holiday rentals and Airbnb in Bennington, VT

Best family friendly Bennington, VT holiday rentals

Among the 48 accommodations in Bennington, VT, here are the 4 best family friendly rentals

1920's Bennington Vermont Guest Barn - Bennington, VT
9.6 207 reviews

1920's Bennington Vermont Guest Barn

apartment, Bennington
This spacious apartment is situated in a peaceful rural setting just outside Bennington, Vermont, within easy reach of the Bennington Museum and Robert Frost Museum, and a short drive from popular ski resorts. It enjoys excellent ratings for location, cleanliness, and overall user experience.
The apartment has three bedrooms and one bathroom, spanning 90 square metres and comfortably accommodating up to seven guests. It comes equipped with a range of modern amenities, including a fully equipped kitchen, a private terrace and garden, and a spa, offering everything you need for a relaxing and enjoyable stay.
Private 1800s Family Farmhouse, Lush Rolling Hills - Bennington, VT
9.9 59 reviews

Private 1800s Family Farmhouse, Lush Rolling Hills

gîte, Bennington
This renovated farmhouse, located just two miles from three local breweries and a 45-minute walk from Bennington College, offers a tranquil escape in a rural setting near Bennington, Vermont. With excellent user, location, and cleanliness ratings, this property provides a comfortable and enjoyable stay for visitors.
The farmhouse, suitable for up to 13 guests, features five bedrooms and three bathrooms, making it ideal for families or groups. Enjoy modern amenities such as a fully equipped kitchen, under-floor heating, high-speed Wi-Fi, and a gas fireplace, while also experiencing the charm of a historic property with stunning views of Mt. Anthony and opportunities for wildlife viewing.
Enjoy Summer & Private, Peace And  Relaxation - Bennington, VT
9.8 42 reviews

Enjoy Summer & Private, Peace And Relaxation

apartment, Hoosick Falls
This property is situated on a private 5-acre plot on the border of New York and Vermont, approximately 30-60 kilometres from several ski resorts, offering a peaceful retreat in a rural setting.
The house can accommodate up to five guests and features two bathrooms, a fully equipped kitchen, and a comfortable living area. You can enjoy a quiet evening by the fire after a day of skiing, relax in the oversized soaking tub, or simply enjoy the peace and quiet of the surrounding nature.
One Of A Kind Cozy Renovated Vt Barn- Where Family, Friends, Couples Gather - Bennington, VT
9.8 17 reviews

One Of A Kind Cozy Renovated Vt Barn- Where Family, Friends, Couples Gather

apartment, Shaftsbury
The Barn Retreat, a self-catering farmhouse near Bennington, Vermont, offers a rural escape approximately 72km from Manchester, providing easy access to local attractions and outdoor activities.
This 195 square metre property sleeps up to 10 guests in three bedrooms and two bathrooms, boasting a rustic-chic interior, a fitness centre, and a spacious great room with a fireplace; nearby activities include skiing at Stratton and Bromley mountains (approx. 72km).

Best pet friendly Bennington, VT holiday rentals

Among the 48 accommodations in Bennington, VT, here are the 4 best pet friendly rentals

Bennington Guest Farmhouse - Bennington, VT
9.7 190 reviews

Bennington Guest Farmhouse

apartment, Bennington
This Victorian farmhouse is located just a mile outside of Bennington, Vermont, making it a convenient base for exploring the town and surrounding countryside. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The farmhouse offers spacious accommodation for up to nine guests, with five bedrooms and two bathrooms spread across 251 square metres. Guests can enjoy a range of amenities, including a fully equipped kitchen, a terrace, a garden, and parking, as well as a gas fireplace and air conditioning for comfort.
Large Country Ranch On 2 Acres - Bennington, VT
9.7 6 reviews

Large Country Ranch On 2 Acres

apartment, Bennington
This charming four-bedroom house is located in Bennington, Vermont, just an hour from Saratoga Springs and its horse races, and within easy reach of ski resorts like Mt. Snow and Bromley Mountain. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The house features a spacious living area with a fireplace, a large wraparound deck with stunning mountain views, and a fully equipped kitchen. Guests can enjoy a range of amenities, including WiFi, a laundry room, a large parking lot, and easy access to various outdoor activities like skiing, hiking, and horse shows in nearby towns.
Breathtaking Mtn Views: Stylish Rustic Retreat! - Bennington, VT
10 31 reviews

Breathtaking Mtn Views: Stylish Rustic Retreat!

house, Pownal
This Pownal holiday home is situated 12 kilometres from the Bennington Battle Monument, offering easy access to this significant historical landmark in Vermont.
The 186 square metre property boasts two bathrooms, a fully equipped kitchen including a dishwasher, free Wi-Fi, and accommodates guests with its two bedrooms and parking.
Karin's Place: Unique And Grand Guest House W/pool - Bennington, VT
9.8 51 reviews

Karin's Place: Unique And Grand Guest House W/pool

apartment, Pownal
This charming apartment is situated in Bennington, Vermont, just 6.5 kilometres from the town of Bennington and 14.5 kilometres from Williamstown, Massachusetts, offering a peaceful retreat in the Vermont countryside. The property has received excellent ratings for its location, cleanliness, and overall guest experience.
The spacious home can comfortably accommodate up to 12 guests in its four bedrooms and two bathrooms. Enjoy a range of amenities including a private pool, hot tub, sauna, a pirate ship playground, a fireplace, and a large backyard, perfect for relaxing and entertaining.

Frequently asked questions about holiday rentals in Bennington, VT

  • What are the must-see sights in Bennington, Vermont?

    Bennington boasts several must-see attractions. The Old First Church, a beautiful example of New England architecture, is a popular spot. The Bennington Battle Monument, a towering structure commemorating a pivotal Revolutionary War battle, offers stunning views. The Robert Hull Fleming Museum at the University of Vermont's Bennington campus showcases diverse art and exhibits. For history buffs, the Bennington Museum is a great choice, detailing the area's rich past.
  • What are the best Airbnb and holiday rentals in Bennington, VT?

    Cozy Modern Sugar House With Spectacular Views, Victorian Home In Bennington - Vermont and Scenic Vermont Studio are the most popular Airbnb and holiday rentals in Bennington, VT among travellers.

  • Are there any unique natural phenomena in Bennington, Vermont?

    While Bennington doesn't have dramatic, unique natural phenomena like geysers, its landscape itself is quite distinctive. The Green Mountains provide breathtaking scenery, offering hiking trails with varied difficulty levels and panoramic views. The area's numerous forests and rivers also provide opportunities for nature lovers to enjoy the peaceful surroundings. Specific locations like Mount Anthony State Park offer great hiking and scenic overlooks.
  • What are the most popular Airbnbs in Bennington, VT?

    Among the Airbnbs in Bennington, VT, Cozy Modern Sugar House With Spectacular Views, Scenic Vermont Studio and Cooper's Place are the most popular ones.

  • What essentials should you bring along for a trip to Bennington, Vermont?

    Pack for all types of weather, as Vermont's climate can be unpredictable. Comfortable walking shoes are a must for exploring the town and surrounding areas. Layers of clothing are essential, including a waterproof jacket and warm sweater, even during summer. Don't forget sunscreen, insect repellent, and a hat for sun protection. A reusable water bottle is also highly recommended.
  • What are the best holiday rentals with a pool in Bennington, VT?

    The best holiday rental with a pool in Bennington, VT is Historic Home In Old Bennington - Vermont.

  • What famous events or festivals are happening in Bennington, Vermont?

    Bennington hosts several events throughout the year. The Bennington Battle Day Parade, a significant historical commemoration, is a notable annual event. Local farmers' markets offer a taste of regional produce and crafts. Check local listings for smaller, community-based events that may be happening during your visit.
  • What are the best rentals for families and kids in Bennington, VT?

    The best rentals for families and kids in Bennington, VT are Two Brooks Lodge, Suite Sunset 311 Rice Lane Bennington Vt and Perfect For Leaf Peeping W\/bar Room - Hot Tub.

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Bennington, Vermont?

    A daily budget will vary greatly depending on your travel style. Accommodation costs can range from £50 to £200 per night, food can range from £25 to £75 per day, and activities and transportation can add another £20 to £50 per day. Therefore, a reasonable daily budget could range from £100 to £300 per person, depending on your choices.
  • What are the best rentals or Airbnbs with a jacuzzi in Bennington, VT?

  • Where can you find the best restaurants serving local dishes in Bennington, Vermont, and what are the must-try specialties?

    Bennington has several charming restaurants. The Walloomsac Inn is a well-regarded option, known for its upscale dining experience. For more casual fare, there are various cafes and pubs around town. Local specialties often feature Vermont cheese, maple syrup, and seasonal produce. Look for dishes incorporating these ingredients for an authentic taste of the region.
  • What are some less-famous attractions in Bennington, Vermont that are worth a visit?

    Beyond the main attractions, explore the charming streets of downtown Bennington. Discover hidden gems like local art galleries and independent shops. The Bennington College campus is architecturally interesting and worth a stroll. Consider visiting some of the smaller, local museums or historical societies in the area.
  • What are the best activities for engaging with locals and understanding their culture in Bennington, Vermont?

    Visiting local farmers' markets is a great way to interact with residents and learn about local produce and traditions. Attending community events or local festivals allows for engaging with the community. Striking up conversations with staff at local businesses or restaurants is another easy way to learn about daily life in Bennington.
  • What unique natural landscapes and terrain features can travellers explore in Bennington, Vermont?

    Bennington's landscape is characterised by the Green Mountains, offering hiking trails and scenic overlooks. The area's forests and rivers provide opportunities for outdoor activities such as hiking, fishing, and kayaking. Mount Anthony State Park is a great starting point for exploring the natural beauty of the area.
  • How many days are ideal for a visit to Bennington, Vermont, and what are some itinerary suggestions?

    Two to three days is a good amount of time to experience Bennington's highlights. Day one could focus on historical sites like the Bennington Battle Monument and the Bennington Museum. Day two could involve exploring the natural surroundings, perhaps with a hike in Mount Anthony State Park. A third day could be dedicated to exploring the town, visiting local shops and restaurants.

Nearby regions

Best Bennington, VT holiday rentals with a pool

Among the 48 accommodations in Bennington, VT, here are the 1 best rentals with a pool

Karin's Place: Unique And Grand Guest House W/pool - Bennington, VT
9.8 51 reviews

Karin's Place: Unique And Grand Guest House W/pool

apartment, Pownal
This charming apartment is situated in Bennington, Vermont, just 6.5 kilometres from the town of Bennington and 14.5 kilometres from Williamstown, Massachusetts, offering a peaceful retreat in the Vermont countryside. The property has received excellent ratings for its location, cleanliness, and overall guest experience.
The spacious home can comfortably accommodate up to 12 guests in its four bedrooms and two bathrooms. Enjoy a range of amenities including a private pool, hot tub, sauna, a pirate ship playground, a fireplace, and a large backyard, perfect for relaxing and entertaining.

Best Bennington, VT holiday rentals with parking

Historic 1769 Vermont Home Near Manchester - Bennington, VT
10 79 reviews

Historic 1769 Vermont Home Near Manchester

apartment, Bennington
The Henry House is a historic home situated on 25 acres of meadows and mountains, overlooking the Walloomsac River and the Henry Covered Bridge, a short distance from Bennington's historic downtown area. This property has received excellent ratings for its location, cleanliness and overall experience.
The house has a variety of rooms, including a cozy first-floor room, a grand ballroom/bridal suite, and a spacious upstairs room with exposed woodwork, accommodating up to 10 guests. Amenities include a fully equipped kitchen, a garden, parking, and a private bathroom for several rooms.
Mount Anthony Cabin - Bennington, VT
9.9 99 reviews

Mount Anthony Cabin

cabin, Bennington
This Bennington holiday lodge is situated at the foot of Mount Anthony, a 16km drive from Bennington's town centre and near a 300-acre Christmas tree farm offering hiking trails.
The 97 square metre self-catering property boasts a spacious open-plan layout, sleeping four guests across two bedrooms, and features a fully equipped kitchen, wrap-around deck, and satellite Wi-Fi.
Walkable Modern 2br In Downtown - Left Unit - Bennington, VT
9.7 54 reviews

Walkable Modern 2br In Downtown - Left Unit

apartment, Bennington
This Bennington apartment is conveniently located just a short distance from supermarkets like Walmart and Hannaford, as well as a range of shops, making it easy to pick up essentials and explore the local area. The surrounding area also offers opportunities for outdoor recreation, with ski areas, mountains, hiking trails and lakes all within easy reach.
This comfortable self-catering property is ideal for families or groups of up to six people. The apartment has a kitchen with a fridge, freezer and microwave oven, as well as air conditioning, parking, and internet access.
5br Rustic Mountain Sanctuary Dome Home - Bennington, VT
9.9 136 reviews

5br Rustic Mountain Sanctuary Dome Home

bubble, Bennington
This unique dome-shaped dwelling is situated just 10km from Bennington, offering a secluded retreat in a scenic mountainous area. The property has received excellent ratings for its cleanliness, location, and overall guest experience.
This unusual accommodation sleeps up to 12 guests and features a fully equipped kitchen, two bathrooms, and a comfortable living space. Enjoy the peaceful surroundings, explore the nearby swimming holes, and take advantage of the on-site steward who can provide local tips and assistance.
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