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Chester – 10 hotels and places to stay
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The Retreat At Norwich Lake, hotel in Chester

Offering free WiFi and a terrace, The Retreat At Norwich Lake is set in Huntington. Springfield, MA is 27 mi away. Free private parking is available on site.

Lovely place! We stayed in a lodge room with an incredibly comfortable king bed. Nice hot shower in nicely appointed bathroom. Beautiful morning view of the lake. Staff super nice and helpful. Since it’s truly a retreat there is no TV in the room, which was surprising but fine - a nice break from noise! Husband watched TNF on his phone to get his football fix. Hope to stay again!
8.5
Scored 8.5
Very Good
Rated very good
8 reviews
Price from$150per night
Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel, hotel in Chester

All rooms feature a flat-screen TV with satellite channels and a private bathroom. Free WiFi is available.

Good price. Lots of activities and amenities.
8.4
Scored 8.4
Very Good
Rated very good
437 reviews
Price from$129per night
The Black Swan Lee - Lenox, Ascend Hotel Collection, hotel in Chester

The Black Swan Inn, Ascend Hotel Collection is conveniently located in the foothills of the Berkshire Mountains.

I liked the view of the lake at our room
8.3
Scored 8.3
Very Good
Rated very good
597 reviews
Price from$90.91per night
Quality Inn, hotel in Chester

Quality Inn has accommodations in Lee. The property is around 6 miles from Tanglewood, 6.2 miles from Tanglewood Musical Center and 7.6 miles from Norman Rockwell Museum.

Nice area , gas station and stores near by.
8.2
Scored 8.2
Very Good
Rated very good
475 reviews
Price from$84.15per night
Pilgrim Inn, hotel in Chester

Located in Lee, between the beautiful Beartown and October Mountain State Forests, Pilgrim Inn is a 20-minute drive from Pitsfield. It features a swimming pool and cozy rooms with free Wi-Fi.

Love the location of this property. We got snowed in and even then we had everything we needed just a few steps away - the supermarket, breakfast and lunch spot, and Starbucks. It’s also in a central location for exploring all of the Berkshires
6.7
Scored 6.7
Pleasant
Rated pleasant
628 reviews
Price from$89per night
Econo Lodge Lee - Great Barrington, hotel in Chester

Located 6 miles from October Mountain State Forest, this Massachusetts hotel features guest rooms with balconies and free Wi-Fi. Americas Best Value Inn Lee serves a daily continental breakfast.

Beds were clean and washroom was clean too. Clean towels and sheets. Had a microwave.
6.0
Scored 6.0
Pleasant
Rated pleasant
223 reviews
Price from$62.10per night
Lakehouse Inn, hotel in Chester

Located in Lee, 1.3 miles from Cranwell Spa & Golf Club, Lakehouse Inn provides accommodations with a garden, free private parking, a shared lounge and a terrace.

The breakfast and the view of the lake.
9.5
Scored 9.5
Exceptional
Rated exceptional
82 reviews
Price from$214per night
Chambery Inn, hotel in Chester

This historic Massachusetts bed and breakfast features free Wi-Fi access and a beautiful front yard. Cable TV and a private bathroom are featured in every uniquely styled room.

It was very cozy and comfortable
9.1
Scored 9.1
Wonderful
Rated wonderful
66 reviews
Price from$199.20per night
Devonfield Inn, hotel in Chester

On 30 acres, this scenic Berkshires bed and breakfast features a heated, seasonal outdoor pool and on-site tennis courts.

Everything ... The place is absolutely beautiful, Doug and Jim are the perfect B&B hosts (as warm, friendly, welcoming and professional as they come.) Jim's breakfasts are amazing and unique. We stayed in room #9 - all the way upstairs - and it was just outstanding in every way. We will definitely be back and will be recommending Devonfield to our friends. It is everything a B&B should be but few live up to or surpass expectations like they do.
9.2
Scored 9.2
Wonderful
Rated wonderful
16 reviews
Price from$319per night
Elm Motel, hotel in Chester

This motel offers refrigerators in each room and free parking. It is located within a 5 - minute drive of Interstate 90 and 10 miles from Six Flags Amusement Park and Blandford Ski Area.

Love spending my money with a family owned business vs giant corporate hotel. Room looked like it had been recently renovated throughout. I travel by motorcycle and prefer a motel where I can park right outside my door. This motel was in a residential setting but not that far from major highways. All 1 level, no noisy kids or adults running the halls and banging doors.
7.3
Scored 7.3
Good
Rated good
188 reviews
Price from$79per night
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