Silk Road covered bridge with trees showing fall colors near Paper Mill Village, Vermont.

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Bennington apartments

Children's area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.6 out of 10, Exceptional, (12 reviews)
"The best stay ever!!! Very clean, great location, super cozy, all the amenities you would need. 5/5 stars, we will be coming back :)"
United States
Carolina I.
The price is AED 337
AED 1,199 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Bromley Retreat
Exterior

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is AED 274
AED 833 total
includes taxes & fees
22 Jun - 23 Jun
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Property grounds

Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (63 reviews)
"This apartment is absolutely beautiful and spacious. It was immaculately clean and provided everything we needed. Communication from Kate was great. We would absolutely stay here again if we are ever in the area. "
United States
Lisa S.
The price is AED 628
AED 889 total
includes taxes & fees
22 Jun - 23 Jun
Spacious apartment in beautiful, historic Arlington VT
Living area

Green Mountain Getaway

Green Mountain Getaway
Bennington
9.6 out of 10, Exceptional, (18 reviews)
"Very clean property. The location was very convenient to the Main Street of Bennington. Easy check in process. Would definitely stay here again! "
United States
Meredith Y.
The price is AED 757
AED 1,504 total
includes taxes & fees
25 Jun - 26 Jun
Green Mountain Getaway
Dining

Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were absolutely amazing. We had a wonderful time. The home is beautiful. The host is very communicative."
United States
Victor G.
The price is AED 797
AED 1,959 total
includes taxes & fees
5 Jul - 6 Jul
Historic Home with Colonial Charm in Manchester
Smart TV

Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
The price is AED 595
AED 1,478 total
includes taxes & fees
22 Jun - 23 Jun
Long Trail House South Wing 2B2B Condo
Private kitchen

Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
The price is AED 761
AED 1,910 total
includes taxes & fees
28 Jun - 29 Jun
Modern Mountain Retreat w/ Chef’s Kitchen
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is AED 229
AED 1,151 total
includes taxes & fees
23 Jun - 24 Jun
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Outdoor dining

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.6 out of 10, Exceptional, (12 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
The price is AED 441
AED 1,041 total
includes taxes & fees
24 Jun - 25 Jun
2-Bdr Apt In Town, By the Water
Exterior

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (33 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
The price is AED 248
AED 525 total
includes taxes & fees
24 Jun - 25 Jun
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Property grounds

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Property grounds

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is AED 393
AED 874 total
includes taxes & fees
22 Jun - 23 Jun
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Property grounds

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
9.0 out of 10, Wonderful, (17 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
The price is AED 698
AED 1,247 total
includes taxes & fees
25 Jun - 26 Jun
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Outdoor dining

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (8 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is AED 452
AED 1,029 total
includes taxes & fees
29 Jun - 30 Jun
Downtown | Waterfront | Walk to Shops
Shower, hair dryer, towels, soap

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Wallingford
10.0 out of 10, Exceptional, (1 review)
"Great stay as always. "
United States
debbie r.
The price is AED 314
AED 640 total
includes taxes & fees
22 Jun - 23 Jun
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Outdoor dining

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (13 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is AED 459
AED 1,016 total
includes taxes & fees
29 Jun - 30 Jun
New Studio In Town, By the Water
Gift shop

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is AED 426
AED 915 total
includes taxes & fees
23 Jun - 24 Jun
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Dining

Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse
Lanesborough
9.4 out of 10, Exceptional, (40 reviews)
"Clean, friendly, but isolated. On premises coffee shop was a bonus."
United States
Karl K.
The price is AED 496
AED 746 total
includes taxes & fees
16 Jul - 17 Jul
Charming Apt in 18th c Berkshire Farmhouse
Gift shop

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (12 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bennington Hotel Reviews

South Shire

South Shire

10/10 Excellent
"South Shire is a quaint Victorian Inn on Elm Street within walking distance to the center of Bennington, VT. The Inn has a family feel and elegance. We traveled as a couple. It was easy to get to sites and enjoy fine restaurants. The Inn is in keeping with the feel of strength of the Bennington community, as a place for artists, musicians, and people's expression generally to thrive. We enjoyed our stay and would recommend South Shire."
Peter 2-night trip
Posted 4 days ago
South Shire

Frequently asked questions

What's it like to stay at an apartment in Bennington?
You can search through 8 apartments in Bennington for your vacation. Why not visit the area's ski slopes and take time to enjoy its majestic mountain landscape while you're here?
Are you thinking about an apartment instead of a traditional hotel?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and is often more spacious than a traditional hotel room. Apartments are a good option for couples who want a more local feel, but also for families who want the conveniences of home.
What's the best apartment I should consider for a stay in Bennington?
Listed below are some of the favorite apartments in the area: Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown: Includes free WiFi, separate dining areas, and Smart TVs. Access to onsite laundry facilities is available on site. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake: Located 18 mi/29 km away in Whitingham. Private balconies, fireplaces, and Smart TVs are included. Free breakfast and onsite laundry facilities are on site. New Studio In Town, By the Water: Located in Williamstown, 12.1 mi/19.5 km from Bennington. Includes free WiFi, private balconies, and sofa beds. Access to onsite laundry facilities is available on site.
How many apartments can I expect to find in Bennington?
Expedia has 8 apartments to book in Bennington.
What will the weather be like when I travel to Bennington?
Weather is only one factor, but it can really affect your travel plans, especially if you are planning a longer stay in Bennington. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Bennington are January, March, February, and December, with each month seeing an average of 8 inches of snowfall.
What are the must-see places to visit in Bennington?
Bennington is well regarded for its mountains and ski slopes. Enjoy the outdoors at Green Mountain National Forest and Harmen Hills Trail, or simply take in cultural attractions like Bennington Museum and Robert Frost Stone House Museum. While here, Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and Bennington Center for the Arts are other places worth a visit.
What's the best way to get to and around Bennington?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Albany Intl. Airport (ALB), which is located 31.7 mi (51 km) away from the heart of the city. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 31.9 mi (51.4 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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