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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
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.

Reasonably priced place that accepts dogs all while providing an exceptional view!!! We enjoy the stay at the Black Swan with staff eager to meet the needs of all customers. The room is a good size, the deck was clean and semi-private, and the view was priceless!
8.3
Scored 8.3
Very Good
Rated very good
600 reviews
Price from$109.65per 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.

All the above, I like.
8.4
Scored 8.4
Very Good
Rated very good
437 reviews
Price from$129per night
Quality Inn, hotel in Chester

Quality Inn has accommodations in Lee. This 2-star inn offers free WiFi. The property is non-smoking throughout and is located 3.5 miles from Cranwell Spa & Golf Club.

Clean and quiet
8.2
Scored 8.2
Very Good
Rated very good
481 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
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.

Like it was clean and near by great restaurants
7.3
Scored 7.3
Good
Rated good
189 reviews
Price from$79per 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.
5.9
Scored 5.9
Above average
Rated okay
224 reviews
Price from$62.99per 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$299per 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.

Staff were extremely accommodating and friendly. Donna went above and beyond on several occasions and was extremely knowledgeable. The inn has everything to make a great stay and we plan on returning in better weather to enjoy the lake 😁
9.5
Scored 9.5
Exceptional
Rated exceptional
84 reviews
Price from$177per 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.
9.3
Scored 9.3
Wonderful
Rated wonderful
15 reviews
Price from$319per night
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