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 Sept - 13 Sept
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 HK$735
HK$2,577 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Bromley Retreat
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 home was spacious, super clean, and in a great location. "
United States
Des C.
The price is HK$1,340
HK$1,896 total
includes taxes & fees
22 Jun - 23 Jun
Spacious apartment in beautiful, historic Arlington VT
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 HK$846
HK$3,116 total
includes taxes & fees
22 Jun - 23 Jun
Historic Home with Colonial Charm in Manchester
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 HK$1,614
HK$3,208 total
includes taxes & fees
25 Jun - 26 Jun
Green Mountain Getaway
Smart TV

Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
The price is HK$1,269
HK$3,152 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 HK$1,264
HK$3,607 total
includes taxes & fees
21 Jun - 22 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 HK$542
HK$2,569 total
includes taxes & fees
30 Jun - 1 Jul
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 HK$940
HK$2,221 total
includes taxes & fees
21 Jun - 22 Jun
2-Bdr Apt In Town, By the Water
Outdoor dining

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is HK$964
HK$2,195 total
includes taxes & fees
30 Jun - 1 Jul
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 HK$670
HK$1,365 total
includes taxes & fees
22 Jun - 23 Jun
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
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.
The price is HK$666
HK$1,594 total
includes taxes & fees
30 Jun - 1 Jul
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
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
The price is HK$635
HK$1,462 total
includes taxes & fees
22 Jun - 23 Jun
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Outdoor dining

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (12 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is HK$940
HK$2,106 total
includes taxes & fees
22 Jun - 23 Jun
New Studio In Town, By the Water
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 HK$980
HK$2,041 total
includes taxes & fees
21 Jun - 22 Jun
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Indoor pool

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is HK$980
HK$2,041 total
includes taxes & fees
21 Jun - 22 Jun
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
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 HK$1,058
HK$1,592 total
includes taxes & fees
16 Jul - 17 Jul
Charming Apt in 18th c Berkshire Farmhouse
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 HK$931
HK$1,985 total
includes taxes & fees
21 Jun - 22 Jun
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Outdoor dining

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (7 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is HK$959
HK$2,017 total
includes taxes & fees
21 Jun - 22 Jun
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Outdoor dining

Okemo | Studio Condo + Loft | Near Slopes + Pool

Okemo | Studio Condo + Loft | Near Slopes + Pool
Jackson Gore Base Area
10.0 out of 10, Exceptional, (2 reviews)
"Very conveinent check in, nice property."
United States
michael
The price is HK$1,642
HK$2,096 total
includes taxes & fees
30 Jun - 1 Jul
Okemo | Studio Condo + Loft | Near Slopes + Pool
A heated pool

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Hancock
9.6 out of 10, Exceptional, (5 reviews)
"Great location on mountain and great communication by unit owner."
United States
Marc F.
The price is HK$1,143
HK$2,248 total
includes taxes & fees
20 Jun - 21 Jun
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
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 2 days ago
South Shire

Find out more about Bennington

Bennington Apartments information

Number of reviews
246
Accommodation
48 Apartments
Lowest Price
HK$1,365
Highest Price
HK$3,607

Frequently asked questions

What's it like to stay at an apartment in Bennington?
There are 8 apartments to choose from in Bennington for your holiday. Why not visit the area's ski slopes and take time to enjoy its majestic mountain landscape while you're here?
Are you considering apartments over traditional hotel rooms?
An apartment features a kitchen for convenient meals, and often has more space than a traditional hotel room. Apartments are a good option for couples who want to live like locals, but also for families who want the conveniences of home.
What's a favourite apartment for a stay in Bennington?
Below are some of the top apartments in the area: Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown: Includes free WiFi, a dining area and a Smart TV . Access to on-site 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 . A balcony, a fireplace and a Smart TV are included . Free breakfast and on-site laundry facilities are on site . Long Trail House Studio at Stratton Mountain Resort: Located in Stratton , 22.3 mi/35.9 km from Bennington. Includes a fireplace and a sofa bed . On-site laundry facilities and 1 hot tub are on site .
How many apartments will I find in Bennington?
Expedia has 8 apartments to book in Bennington.
What will the weather be like during my trip 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 temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Bennington are January, March, February and December, with each month seeing an average of 21 cm 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, Old First Congregational Church 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, NY (ALB-Albany Intl.), which is located 31.7 mi (51 km) from the city centre. 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, you may want to rent a car for your trip.

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