Discover a selection of 1,500 vacation rentals in Bennington County, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $119 per night, and houses and condos are popular options for a stay in Bennington County. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Bennington County

What are the top vacation rentals in Bennington County?

Whether you're organizing your next exciting adventure with pals or a romantic escape with your other half, one of these top vacation rentals in Bennington County is sure to catch your eye:

  • "Charming Vermont Home On 7 Acres W": If you're chasing a comfy living space in Dorset, unpack your bags here. It offers 5 bedrooms and quality amenities including a garage and tennis.
  • "Most Asked For Luxury Home At Stratton Mountain": Located in Bondville, this guest favorite has 5 bedrooms and lots of handy amenities. Free WiFi and a kitchen island are just a couple you'll find here.

For even more great options, use the search bar at the top of the page to find the perfect Bennington County vacation rental for you.

What are the best tiny house vacation rentals in Bennington County?

Punching way above its weight when it comes to charm and innovation, a tiny house vacation rental in Bennington County puts you on the doorstep of big adventure. Close down your gadgets and switch your focus to Mother Nature at one of these pocket-sized stays:

  • You can look forward to a simpler way of living at "Cozy Lakeside Tiny Home, Near Skiing". Amenities at this gem in Whitingham include a toaster and mountain views.
  • Alternatively, base yourself at "Cheerful Tiny Home Cabin Near Hiking". Located in Townshend, this little abode comes with internet services and cookware, dishware and utensils.

Can I find log cabins to rent in Bennington County?

Often surrounded by nature, log cabins offer a lovely retreat from the fast pace of life. If you're ready for some downtime, check out these log cabins to rent in Bennington County:

  • If you'd like to be able to enjoy snowboarding or snowmobiling while you're staying in Bennington County, "Beautiful Lakeview Log Cabin On 60" in Bennington will be a terrific choice.
  • Looking for a Londonderry log cabin with access to awesome activities like snowboarding and hiking and biking? You'll be very happy with "Award - Winning Log Cabin, Top 5 In New England".

What are the top-rated vacation rentals for weekend getaways in Bennington County?

While big extravagant trips are awesome, there's something lovely about embarking on a whirlwind weekend getaway. These properties in Bennington County are perfect for just that:

  • "Beautiful Honeymoon Cottage, By Manchester Center Vermont" - Found in Bennington, this rental property offers its guests handy extras including towels and off-street parking options.
  • "Gracious Vermont Home Epic Mountain Views" - This is another great choice with all the ingredients that make up a delightful weekend away. Expect air conditioning and a pool table at this Bennington property.

Can I find studio apartments for rent in Bennington County?

Studio apartments may be smaller in size, but it's hard to beat their great locations and thrifty price tags. Whether you're traveling by yourself or it's just you and your partner, consider one of these terrific studio apartments in Bennington County:

  • Eat, snooze, relax with friends ... Do it all from the compact yet cleverly designed single space at "Beautiful Honeymoon Cottage, By Manchester Center Vermont". Located in Bennington, a garden and a restaurant dining guide are among the conveniences here.
  • Full of character and offering more privacy than a big hotel, "Quiet, Spacious, Private, Beautiful Views Above Art Studio" is another option with appeal. It's located in Bennington and comes with air conditioning and WiFi.

Can I find short term rentals in Bennington County?

Bennington County has short-term rentals to suit all budgets and tastes. Enjoy some time out in an affordable cabin, a luxurious apartment or whatever else you like. Below are a couple of popular options to consider:

  • Located close to the middle of Bennington, "Beautiful Honeymoon Cottage, By Manchester Center Vermont" is an ideal place for a short-term stay. Set up camp here and head out to explore all the fascinating sights in the area.
  • Alternatively, bunk down for day or two at "Gracious Vermont Home Epic Mountain Views" and discover the highlights of Bennington. This property also caters to short-stay guests and is a good choice if you love being close to the action.

What are the best romantic weekend getaways in Bennington County?

If you want to dazzle your someone special, take them somewhere special! Plan a romantic weekend getaway in Bennington County at one of these retreats and let love bloom:

  • Squeeze in some "us time" at "Charming Vermont Home On 7 Acres W". This Dorset getaway is perfect for romance, with amenities like a fireplace and beauty services to help set the mood.
  • Another amorous option is "Most Asked For Luxury Home At Stratton Mountain" in Bondville. Enjoy perks here including a resort and beauty services, as well as each other's company.

What are the best large group vacation rentals in Bennington County?

If you're planning to take a memorable trip away, don't go alone; take the whole crew. You'll have a lot more fun sharing the experience with the ones you love. These vacation rentals in Bennington County are ideal for larger groups:

  • "Most Asked For Luxury Home At Stratton Mountain": With 5 bedrooms, everyone is invited to this exceptional retreat in Bondville. A water park and a firepit are among the many amenities available here.
  • "Vermont Hillside Retreat": Located in South Shaftsbury, this roomy option has 4 bedrooms and is another popular pick for a get-together with the family. There's a whole lot to keep guests comfortable and content, such as a fireplace and a garden.

What are the best houses for rent with a pool in Bennington County?

In Bennington County, there's no shortage of house rentals where every day can be a pool day. Having a splashing great time will be your main priority at one of these top-notch escapes:

  • Book a stay at "Perfect "goldilocks" Ski And Golf House On Stratton Resort", where the first thing on your itinerary should be taking a dip in the pool. This retreat is located in Stratton and comes with a range of family-friendly amenities, including nearby birdwatching activities and a microwave oven.
  • Leap out of bed and go for an early morning dip at "Ski House At Stratton Mountain" in Bondville. A dishwasher and childrens activities are just two of the many amenities at this exceptional option.

What are the best large family vacation rentals in Bennington County?

Vrbo makes it a cinch to find a great family getaway. With convenient amenities and ample space to stretch out, these large family vacation rentals in Bennington County are some of our best:

  • Make your family catch-up one to remember at "Charming Vermont Home On 7 Acres W". This Bennington property offers 5 bedrooms and can fit up to 11 of your nearest and dearest. Childrens activities and coffee and tea making facilities are among the amenities to make use of here.
  • "Most Asked For Luxury Home At Stratton Mountain" in Bondville will also roll out the welcome mat you and the fam. Accommodating up to 16 guests, this retreat features 5 bedrooms, a stereo and a foosball table.

Looking for some family-friendly entertainment? Vermont Summer Festival is one of the many exciting attractions you'll find dotted around Bennington County.

Explore destinations around Bennington County

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