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4-star hotels in Bennington
This shortlist gathers the 4-star hotels and lodges around Bennington for travellers who want a real Vermont town with the Taconics and Mount Snow within easy reach. It suits couples after a quiet bolthole, families needing space, and skiers chasing powder.
Staying in Bennington
Bennington anchors the southwest corner of Vermont at the junction of US-7 and VT-9. The 306-foot Battle Monument, the Bennington Museum's Grandma Moses collection, Old First Church and a walkable main street fill a comfortable day. It is a working town rather than a resort village, so you trade the picture-postcard streets of a Woodstock for lower-key lodging and the same mountains next door. A car is necessary, since there is no passenger rail and the nearest airport, Albany International, is about an hour away.
The properties here spread across the area rather than sitting in one cluster. The Four Chimneys Inn, South Shire and Bromley Farm Ski House carry Bennington addresses, close to the historic district and the town's sights. The Wilmington group — Mountain Retreat, Private Wooded Cabin 7 Mi to Mount Snow, Log Ski Lodge and Crooked Ear Cabin — sits up the valley toward Mount Snow, better for skiers than for strolling to the monument. Stargazing Daydreamer lies in Arlington to the north, handy for the Battenkill valley. Couples tend to favour the inns and cabins, families the larger lodges with pools and kitchens, and skiers anything within reach of the mountain.
The shortlist
Ranked by hotel class, then guest rating and number of reviews.
The Four Chimneys Inn
21 West Road, Bennington, United States
Why stay hereSet on West Road in Bennington, this 4-star inn is a straightforward base for exploring the area. Guest reviews are not available, so judge it on the address and positioning rather than ratings. Best for travellers who want a quiet, simple stay close to Bennington's centre and don't need extra facilities on site.
See The Four Chimneys InnMountain Retreat
6 Shincracker Way, Wilmington, United States
Best for: Families · Drivers
- Indoor pool
- Free car parking
- Pool bar
Why stay hereThis 4-star Wilmington retreat on Shincracker Way suits guests who want plenty to do on site. An indoor pool and a games room stand out among the many amenities, and there is a Jacuzzi as well. With skiing and a beach nearby, active travellers and families can fill their days easily without leaving the property's orbit.
See Mountain RetreatPrivate Wooded Cabin 7 Mi to Mount Snow
21 Beebe Road, Wilmington, United States
Best for: Drivers · Pool and spa
- Spa
- Parking
- Pets allowed
Why stay hereA 4-star wooden cabin on Beebe Road, 7 mi from Mount Snow, ideal for skiers who prefer privacy. It comes with a kitchen, a fireplace and a spa, plus Wi-Fi. Pets are allowed, which makes it a practical choice for travellers bringing a dog. Couples or small groups wanting a self-contained wooded stay will find it well suited.
See Private Wooded Cabin 7 Mi to Mount SnowSouth Shire
124 Elm St, Bennington, United States
Why stay hereOn Elm St in Bennington, this 4-star property offers a central location within the town. No guest rating or listed facilities are available, so there is little to say beyond the address and class. It suits visitors who simply want a Bennington base and will sort out their own meals and activities.
See South ShireBromley Farm Ski House
Bromley Farm Road, Bennington, United States
Best for: Drivers
- Free car parking
- Kitchen
- Air conditioning
Why stay hereThis 4-star ski house on Bromley Farm Road in Bennington is built for group stays. A full kitchen, a fireplace and a washing machine cover the practical side, and there is free car parking. Guests with their own transport heading for the nearby slopes will appreciate having space and self-catering rather than hotel services.
See Bromley Farm Ski HouseLog Ski Lodge
162 Binney Brook Road, Wilmington, United States
Best for: Pool and spa
- Outdoor pool
- Sauna
- Fitness Center
Why stay hereOn Binney Brook Road in Wilmington, this 4-star log lodge leans into leisure: an outdoor pool, a sauna and a restaurant are all on site. Skiing and fishing are available nearby, and a fitness centre and Jacuzzi round out the options. Good for guests who want a resort-style stay with dining handled for them.
See Log Ski LodgeCrooked Ear Cabin
193 Chimney Hill Road, Wilmington, United States
Best for: Drivers · Pool and spa
- Spa
- Free car parking
- Pets allowed
Why stay hereCrooked Ear Cabin on Chimney Hill Road is a 4-star Wilmington property that welcomes pets and has a spa and a fireplace. A kitchen and Wi-Fi add everyday convenience, and there is free car parking. The combination of self-catering, a tennis court and pet-friendly rules suits families or groups travelling by car with a dog.
See Crooked Ear CabinStargazing Daydreamer
46 Limerick Lane, Arlington, United States
Best for: Travelling with pets
- Pets allowed
- Kitchen
- Beach nearby
Why stay hereThis 4-star Arlington property on Limerick Lane invites stargazing and gathers guests who want both comfort and activity. A kitchen, air conditioning and a patio are provided, and pets are allowed. Skiing, fishing and a playground nearby give children and adults something to do, making it a reasonable fit for families on an outdoor holiday.
See Stargazing Daydreamer
How to choose
For families
Families get the most room and the most to do at Mountain Retreat, Log Ski Lodge and Stargazing Daydreamer.
For skiers
Skiers should look at the Wilmington addresses. Private Wooded Cabin 7 Mi to Mount Snow is named for its proximity to the mountain, and Mountain Retreat, Log Ski Lodge and Crooked Ear Cabin all list skiing among their facilities. Log Ski Lodge and Mountain Retreat add a sauna and a pool for après-ski.
Mountain Retreat · Log Ski Lodge · Private Wooded Cabin 7 Mi to Mount Snow · Crooked Ear Cabin
For couples
Couples after a quieter stay can choose The Four Chimneys Inn or South Shire in Bennington, both close to the historic district. Crooked Ear Cabin and Private Wooded Cabin 7 Mi to Mount Snow offer fireplaces and spa facilities in the woods, and the latter welcomes pets.
The Four Chimneys Inn · South Shire · Crooked Ear Cabin · Private Wooded Cabin 7 Mi to Mount Snow
For pets
Each also provides practical extras such as a kitchen, washing machine and free parking, so a stay with a dog needs less compromise.
Private Wooded Cabin 7 Mi to Mount Snow · Crooked Ear Cabin · Stargazing Daydreamer
Where to stay in Bennington
Wilmington
Wilmington lies up the valley toward Mount Snow, which makes it the base for skiers rather than for the monument. Mountain Retreat, Private Wooded Cabin 7 Mi to Mount Snow, Log Ski Lodge and Crooked Ear Cabin all carry Wilmington addresses, and each lists skiing or a mountain connection among its facilities.
Our picks here: Mountain Retreat · Private Wooded Cabin 7 Mi to Mount Snow · Log Ski Lodge · Crooked Ear Cabin
Arlington
Arlington sits north of Bennington in the Battenkill valley, reached by US-7 on the way toward Manchester. Stargazing Daydreamer on Limerick Lane is the property here, listing a playground, kitchen and pets allowed, and serves as a quiet northern base for the surrounding countryside.
Our picks here: Stargazing Daydreamer
Plan your stay
Getting there and around
Bennington sits at the junction of US-7 and VT-9 in the southwest corner of the state, with US-7 running north toward Manchester and Rutland and VT-9, the Molly Stark Trail, crossing east to Brattleboro. Albany International (ALB) is the nearest airport at about an hour. There is no passenger rail, and the interstates are well to the east and west, so a car is necessary.
When to go
The site's own text gives no particular season for Bennington, but the town's sights — the Battle Monument, Old First Church, the museum and the North Bennington bridges — fill a full day without rushing and half a day if you skip the museum. Because a car is necessary and the interstates lie well to the east and west, travel is easiest when the mountain roads are clear; the ski-oriented Wilmington properties point to winter as their own high season.
Things to do near Bennington
Questions, answered
Which of these hotels is closest to the centre of Bennington?
The Four Chimneys Inn on West Road and South Shire on Elm St both carry Bennington addresses and sit near the historic district, monument and main street. The Wilmington and Arlington properties are further out and better suited to a car-based stay.
Do any of these hotels allow pets?
Yes. Private Wooded Cabin 7 Mi to Mount Snow, Crooked Ear Cabin and Stargazing Daydreamer all list pets allowed among their facilities. None of the Bennington properties on this shortlist state that pets are welcome.
Which hotels have a pool?
Mountain Retreat lists an indoor pool, a swimming pool and a pool bar. Log Ski Lodge lists both an outdoor pool and a swimming pool, plus a sauna. No other property on this shortlist mentions a pool.
Are there hotels with spa facilities?
Private Wooded Cabin 7 Mi to Mount Snow and Crooked Ear Cabin both list a spa. Log Ski Lodge lists a sauna and a jacuzzi instead. The Bennington properties on this shortlist do not list spa or wellness facilities.
Where should families stay?
Mountain Retreat, Log Ski Lodge and Stargazing Daydreamer are the strongest family choices. Mountain Retreat adds family rooms, a games room and table tennis; Log Ski Lodge has a playground and outdoor pool; Stargazing Daydreamer lists a playground and a sofa bed.
Which hotels are best for skiing?
The Wilmington properties are the ski bases. Private Wooded Cabin 7 Mi to Mount Snow is named for its proximity to the mountain, and Mountain Retreat, Log Ski Lodge and Crooked Ear Cabin all list skiing among their facilities.
Do these hotels offer free parking?
Free car parking is listed at Mountain Retreat, Bromley Farm Ski House and Crooked Ear Cabin. Parking is listed as a facility at Private Wooded Cabin 7 Mi to Mount Snow and Log Ski Lodge as well. The Four Chimneys Inn and South Shire list no facilities.
Which is the highest-rated hotel on this shortlist?
The data provided gives no guest ratings or review counts for any of these properties, so no single hotel can be named as the top pick. Every property on the shortlist is rated 4 stars, and the choice comes down to location and facilities.