We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
View map
Sponsored by:
Accommodation
Price per night
Location
Any Distance
from
Style
  • Sort by:
  • Traveller Ranked
  • Best Value
  • Lowest price
  • Distance
Updating list...
See all hotels in or near Chesterfield
LakeHouse Inn
SAVE US$ 32
US$ 200
Orbitz.com
US$ 168
View Deal
35.3 km from Chesterfield
  • Free Wifi
  • Free Parking
View hotel details
Collapse hotel details
Reviewed 2 days ago

I can't say enough about our three wonderful nights at the Lake House Inn. The beds and linens were great. The room with balcony and lake view were spectacular. And then came a superb Three course...More

Reviewed 2 days ago

My husband and I stayed here for a fall leaf peeping excursion. Our room was modern and spacious with a gorgeous view of the lake. There were thoughtful charging places for devices and clever spots...More

Hotel website
615 Laurel St, Lee, MA 01238-9180
(413) 207-9390
Free Parking
Free Wifi
Breakfast included
4.0 Star Hotel
Official Hotel
US$ 178
View Deal
34.5 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
View hotel details
Collapse hotel details
Reviewed 3 days ago

Eat, socialize and get taken excellent care of. Beautiful large room furnished with care and excellent taste in the tradition of local culture. The restaurant is large, beautiful, mostly quiet...More

Reviewed 6 days ago

Hotel on Fourth was a delight beyond our wildest expectations! It is a gem in the middle of an area that will hopefully experience a renaissance over time. The hotel is beautifully furnished; the...More

Hotel website
297 North St, Pittsfield, MA 01201-4602
(413) 358-4440
Room Service
Free Parking
Restaurant
Bar/Lounge
Free Wifi
Fitness centre
3.5 Star Hotel
Hampton Terrace Bed and Breakfast Inn
SAVE US$ 23
US$ 245
Official Site
US$ 222
View Deal
36.3 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
Offers & AnnouncementsLow Midweek Rates! 🔖
Savings alert: 11% below average rate

The price you found is 11% lower than this hotel's average rate of US$ 249/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

View hotel details
Collapse hotel details
Reviewed 4 days ago

Enjoyed our stay here. Stayed the main house which was warm and felt like we were in a home. Loved hearing about the history of the House. Breakfast was simple but filing. Enjoyed being able to spend...More

Reviewed 1 week ago

Yes, Joe and I have been going back to Lenox and the Hampton Terrace for 10 years. We always choose to stay with Susan, Stan and Holly, because their welcoming way, proves he has Southern charm and...More

Hotel website
91 Walker St, Lenox, MA 01240-2719
+1 844-336-0756
Free Parking
Pool
Free Wifi
Breakfast included
4.0 Star Hotel
Homewood Suites Holyoke-Springfield\/North
Homewood
US$ 178
View Deal
29.8 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
View hotel details
Collapse hotel details
Reviewed 5 days ago

The hotel was very clean and located very close to the highway and downtown Springfield. I wasn't very impressed with the breakfast selection compared to other homewood Suites I've stayed in, but...More

Reviewed 1 week ago

Wonderful staff, quiet rooms, excellent furnishings, super comfortable bed made my extended stay all that I had hoped for. Location was hard to beat...just blocks off of Route 91 and easy access to...More

Hotel website
375 Whitney Ave, Holyoke, MA 01040-2855
+1 855-605-0320
Pool
Free Parking
Fitness centre
Free Wifi
Breakfast included
3.0 Star Hotel
Old Sturbridge Inn & Reeder Family Lodges
SAVE US$ 12
US$ 122
Travelocity
US$ 110
View Deal
69.4 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
Special RateFall Escape
View hotel details
Collapse hotel details
Reviewed 4 days ago

We took advantage of the Mid week special ($109 per night) and stayed in the Oliver Wright home. We were delighted to find such a large, gorgeous room with history written all over it. The...More

Reviewed 1 week ago

I needed to stay in an early home, and was thrilled to be with Rufus Porter murals. Over the years the Oliver Wight House has seen changes, but original flooring, woodwork, and murals in the entry...More

Hotel website
369 Main St, Sturbridge, MA 01566-1054
(508) 213-9736
Pool
Free Parking
Free Wifi
Breakfast included
3.0 Star Hotel
SAVE US$ 12
US$ 213
Booking.com
US$ 201
View Deal
26.1 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
Offers & AnnouncementsMidweek Date Night Pkg 🍂
Savings alert: 38% below average rate

The price you found is 38% lower than this hotel's average rate of US$ 324/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

View hotel details
Collapse hotel details
Reviewed 4 days ago

Such a cozy quaint inn in the heart of a historic town. We loved our room, it was furnished so pretty, and the bed was amazing! We ate at the inns restaurant the two nights we were there. The food...More

Reviewed 5 days ago

The Deerfield Inn is a lovely surprise in the middle of nowhere Massachusetts. The rooms are clean and, for the most part, quite large. The staff are incredibly friendly and accommodating...More

Hotel website
81 Old Main St, Deerfield, MA 01342-5005
(413) 344-2187
Restaurant
Free Parking
Free Wifi
Bar/Lounge
Breakfast included
Room Service
4.0 Star Hotel
Briarcliff Motel
Travelocity
US$ 101
View Deal
43.8 km from Chesterfield
  • Free Wifi
  • Free Parking
View hotel details
Collapse hotel details
Reviewed 3 weeks ago

The Briarcliff is well-located and is reasonably priced. The innkeepers are friendly, helpful and solicitous. The included breakfast is great. We also enjoy the whimsical decorating details. We...More

Reviewed 3 weeks ago

This motel, set well back from the main road between Great Barrington and Stockbridge, capitalizes on the thriving ‘locavore’ movement in this area, with fabulous breakfasts of locally sourced dairy...More

Hotel website
506 Stockbridge Rd, Great Barrington, MA 01230-1296
(413) 207-9420
Free Parking
Free Wifi
Breakfast included
2.0 Star Hotel
Hampton Inn & Suites Hartford-Manchester
Hampton.com
US$ 160
View Deal
69.2 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
View hotel details
Collapse hotel details
Reviewed 2 days ago

Staff was very accommodating. Available for you at all times. Breakfast food were very diverse in assortment. All staff members greeted you as if you were a VIP guest. I will definitely stay here...More

Reviewed 6 days ago

Friendly staff at check-in, breakfast, and check-out. Clean room. Conveniently located just off I-84. There's a craft burger restaurant just across the parking lot. Plenty of other food options...More

Hotel website
1432 Pleasant Valley Rd, Manchester, CT 06042-8761
+1 855-605-0317
Pool
Free Parking
Free Wifi
Fitness centre
Breakfast included
2.5 Star Hotel
Hampton Inn & Suites Springfield\/Downtown
Hampton.com
US$ 142
View Deal
39.5 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
View hotel details
Collapse hotel details
Reviewed 6 days ago

The hotel is very easy to find and get to as it is right off the highway. The front desk check-in was very quick and easy with no lines and the front-desk associates were very helpful. There is a...More

Reviewed 1 week ago

After a long day at Six Flags we checked into the hotel late. Both of our rooms were modern and updated with a lot of outlets to plug in phones and devices. Large TV and beds were great. Room was...More

Hotel website
851 E Columbus Ave, Springfield, MA 01105-2534
+1 855-605-0317
Pool
Free Parking
Free Wifi
Breakfast included
Fitness centre
2.5 Star Hotel
The Porches Inn at MASS MoCA
Official Hotel
US$ 200
View Deal
41.3 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
Special OfferTake a Hike Package
View hotel details
Collapse hotel details
Reviewed yesterday

It was a short stay and we really love the history and style of the building, The location is perfect. MASS MoCA is right cross the street and nice restaurants are in walking distance. Room is clean...More

Reviewed 3 days ago

An historic Registry property lovingly restored, Porches has tons of charm with the added benefit of spa amenities and great service. We enjoyed the year-round, outdoor swimming pool and hot-tub, and...More

Hotel website
231 River St, North Adams, MA 01247-3201
(413) 650-1575
Pool
Free Parking
Free Wifi
Breakfast included
Bar/Lounge
Fitness centre
3.5 Star Hotel
Southbridge Hotel And Conference Center
SAVE US$ 3
US$ 103
Travelocity
US$ 100
View Deal
75.9 km from Chesterfield
  • Free Wifi
  • Free Parking
View hotel details
Collapse hotel details
Reviewed 1 week ago

Everything about the hotel from the front desk staff to the restaurant to the facilities was excellent. Very accommodating in every respect. A good find when visiting the area. Don't hesitate because...More

Reviewed 1 week ago

I was skeptical as to how well an old American Optical factory and office building could be turned into a conference center and hotel, and I was very pleasantly surprised! The rooms were spacious...More

Hotel website
14 Mechanic St, Southbridge, MA 01550-2570
(508) 252-0030
Free Parking
Free Wifi
Pool
Restaurant
Fitness centre
Bar/Lounge
Room Service
3.0 Star Hotel
Hampton Inn & Suites Hartford\/Farmington
Travelocity
US$ 194
View Deal
76.1 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
View hotel details
Collapse hotel details
Reviewed yesterday

Great stay at this Hampton! Safe & quiet location, near the highway. The hotel was very clean, the bed was comfortable, the towels were bright white & soft. The staff was very friendly & offerred...More

Reviewed 1 week ago

If you are looking for a very nice hotel, this is the one for you. The staff is professional and polite. The rooms are spotlessly clean and smell great. The breakfast in the morning, included with...More

Hotel website
301 Colt Hwy, Farmington, CT 06032-3080
+1 855-605-0317
Pool
Free Parking
Free Wifi
Fitness centre
Breakfast included
2.5 Star Hotel
Hilton Garden Inn Hartford South\/Glastonbury
GardenInn.com
US$ 165
View Deal
76.6 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
Savings alert: 13% below average rate

The price you found is 13% lower than this hotel's average rate of US$ 190/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

View hotel details
Collapse hotel details
Reviewed yesterday

Nicely appointed lobby, ample parking front and back, good breakfast buffet with made to order selections too. Bar area and TVs' to watch the games. Good shopping mall across the street with many...More

Reviewed 1 week ago

This is not a five star hotel but in its class it is a six! I and my wife stayed there this past weekend for a wedding that was not on premises - but many family members and friends (20+) stayed at...More

Hotel website
85 Glastonbury Blvd, Glastonbury, CT 06033-4401
+1 855-618-4697
Pool
Free Parking
Restaurant
Fitness centre
Free Wifi
Room Service
Bar/Lounge
3.0 Star Hotel
Hampton Inn & Suites Hartford\/East Hartford
Booking.com
US$ 125
View Deal
71.3 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
View hotel details
Collapse hotel details
Reviewed 5 days ago

Another good Hampton experience. Price is considerably less than nearby Manchester, so if you don't need easy access to restaurants and mall shopping, this is a great choice. It's a little tricky...More

Reviewed 6 days ago

Needed a convenient place to stop along the way from NYC to Boston, and this was just the place. Comfortable, please, affordable, and free breakfast to boot (the latter is not fancy, but when you're...More

Hotel website
351 Pitkin Street, East Hartford, CT 06108-6221
+1 855-605-0317
Pool
Free Parking
Free Wifi
Fitness centre
Breakfast included
2.5 Star Hotel
Hampton Inn Chicopee\/Springfield
Booking.com
US$ 142
View Deal
32.6 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
View hotel details
Collapse hotel details
Reviewed 3 days ago

When you travel as much as I do, especially to the same city, it is very important to feel at home. I live in NC but I am from NH. So I am a huge Boston area sports fan. Everyone that works the front...More

Reviewed 1 week ago

I would highly recommend this location. The staff was excellent and the room was very clean. The complimentary breakfast was also very good. The only disappointment was the lack of rules in the pool...More

Hotel website
600 Memorial Dr, Chicopee, MA 01020-5019
+1 855-605-0317
Pool
Free Parking
Free Wifi
Fitness centre
Breakfast included
2.5 Star Hotel
Hilton Garden Inn Troy
SAVE US$ 35
US$ 167
GardenInn.com
US$ 132
View Deal
78.2 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
View hotel details
Collapse hotel details
Reviewed 2 days ago

This was a last stop on our senior 55+ vacation . We felt safe and very comfortable in the Hilton in Troy. The room was comfortable and large. We had a big bathroom handicap. Towels are large and...More

Reviewed 2 days ago

We stayed at this hotel because a family wedding was held here. The food was fabulous and the staff was exceptional. This Hilton Garden Inn provided the perfect setting for my family to make great...More

Hotel website
235 Hoosick St, Troy, NY 12180-2428
+1 855-618-4697
Pool
Free Parking
Free Wifi
Fitness centre
Restaurant
Bar/Lounge
Room Service
3.0 Star Hotel
Hampton Inn & Suites Greenfield
SAVE US$ 43
US$ 198
Hampton.com
US$ 155
View Deal
28.2 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
View hotel details
Collapse hotel details
Reviewed yesterday

We had a mini family reunion in the Greenfield area and chose to stay at this property. It has a wonderful friendly atmosphere, is comfortable, clean, welcoming and has a great breakfast. There was a...More

Reviewed yesterday

staff was great and Hilton team attended to our needs. great facilities and location. we enjoyed the ease of access to the Mohawk Trail as well as ease of access to markets and highway. we recommend...More

Hotel website
184 Shelburne Rd, Greenfield, MA 01301-9624
+1 855-605-0317
Pool
Free Parking
Free Wifi
Fitness centre
Breakfast included
2.5 Star Hotel
Hartford Marriott Downtown
Travelocity
US$ 378
View Deal
71.4 km from Chesterfield
  • Free Wifi
  • Pool
Special offer
Special OfferEarn a Free Night
View hotel details
Collapse hotel details
Reviewed 1 week ago

I last was here in 2012 and recently stayed the end of July 2017. They have totally changed the decor and it looks really great. I like that they have couches scattered throughout the lobby and...More

Reviewed 1 week ago

Situated just off the highway and right next to the Science Centre, I was close to everything I went to CT for. Short drive to West Hartford area or a 15 minute drive to the mall. Parking was a...More

Hotel website
200 Columbus Blvd, Hartford, CT 06103-2807
Restaurant
Pool
Fitness centre
Room Service
Free Wifi
Bar/Lounge
Spa
4.0 Star Hotel
MAPLE TERRACE MOTEL
Booking.com
View Deal
45.4 km from Chesterfield
  • Free Wifi
  • Free Parking
View hotel details
Collapse hotel details
Reviewed 1 week ago

We had a nice time on our trip to Williamstown. The location of the motel is excellent for access to many local attractions. Visited museums and restaurants in town. Travelled to VT also - easy...More

Reviewed 1 week ago

I just spent a night at the Maple Terrace Motel while I was passing through Williamstown on the way to a wedding. I enjoyed it so much I wish I could have stayed longer. The room was spotless...More

555 Main St, Williamstown, MA 01267-2612
Pool
Free Parking
Free Wifi
Breakfast included
2.5 Star Hotel
Hampton Inn Bennington
SAVE US$ 44
US$ 206
Hampton.com
US$ 162
View Deal
65.4 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
View hotel details
Collapse hotel details
Reviewed 6 days ago

Close to the green mountains, friendly staff and clean rooms. Loved their little extra evening Vermont cheese and warm apple cider treats. Expensive to stay in October due to the fall...More

Reviewed 2 weeks ago

This was the beginning of my bucket list trip and the first stop on the journey and it did not disappoint. While we were there the weather was chilly and it was really nice to come into the lobby to...More

Hotel website
51 Hannaford Sq, Bennington, VT 05201-1603
+1 855-605-0317
Pool
Free Parking
Free Wifi
Fitness centre
Breakfast included
2.5 Star Hotel
Hampton Inn Hartford \/ Airport
Hampton.com
US$ 148
View Deal
54.9 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
View hotel details
Collapse hotel details
Reviewed yesterday

I stay at this hotel frequently for early morning flights out of Bradley. I have had different experiences here, but our stay this past weekend was wonderful. Excellent staff on duty, professional...More

Reviewed 2 days ago

I spent a quick overnight here before an early morning flight. As a woman traveling alone, I always appreciate a sense of security and definitely appreciate quality accommodations. I trust in Hilton...More

Hotel website
2168 Poquonock Ave, Windsor, CT 06095-1238
+1 855-605-0317
Pool
Free Parking
Free Wifi
Breakfast included
Fitness centre
Spa
2.5 Star Hotel
Hilton Garden Inn Lenox Pittsfield
GardenInn.com
US$ 122
View Deal
34.8 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
View hotel details
Collapse hotel details
Reviewed yesterday

This was a nice hotel. Typical of the new modern hotels and the beds where very good I have a temperpedic and miss it very much on trips but this was okay. Breakfast was a nice surprise but other...More

Reviewed 3 days ago

Nice hotel at a great price. We were in Berkshires for our son’s wedding. The hotel was centrally located for all of our events. The rooms are very nice, the staff is very friendly and helpfu. The...More

Hotel website
1032 South St, Pittsfield, MA 01201-8225
+1 855-618-4697
Pool
Room Service
Free Parking
Restaurant
Bar/Lounge
Free Wifi
Fitness centre
3.0 Star Hotel
D. Hotel & Suites
Official Website
US$ 127
View Deal
23.6 km from Chesterfield
  • Free Wifi
  • Free Parking
View hotel details
Collapse hotel details
Reviewed yesterday

Excellent accommodations and enjoyed the adjoining restaurant tremendously. Staff friendly and helpful with local attractions and directions. Housekeeping responded quickly to requests. Enjoyed the...More

Reviewed 3 days ago

Excellent hotel. Staff very friendly and room was very nice!! The hotel was very clean and service exceptional. The food was delicious and the breakfast room was perfect for a quick bite before...More

1 Country Club Rd, Holyoke, MA 01040-9609
Fitness centre
Free Parking
Free Wifi
Pool
Restaurant
Breakfast included
Room Service
Bar/Lounge
3.0 Star Hotel
Canyon Ranch in Lenox
36.3 km from Chesterfield
  • Free Wifi
  • Free Parking
Special offer
View hotel details
Collapse hotel details
Reviewed 1 week ago

What an amazing day! Staff is absolutely fabulous from the second you drive up until the second you leave. Food is amazing. Everything was very clean and comfortable. The zipline is awesome!!!! Staff...More

Reviewed 1 week ago

From the moment we arrived the attention paid to us was just incredible. It was my first time to Canyon Ranch, loved our room, big spacious and very clean. I enjoyed every lecture as they were...More

Hotel website
165 Kemble St, Lenox, MA 01240-2817
+1 855-775-9780
Pool
Restaurant
Free Parking
Fitness centre
Free Wifi
Spa
Breakfast included
Garden Gables Inn
TripAdvisor
US$ 195
View Deal
36.5 km from Chesterfield
  • Free Wifi
  • Free Parking
View hotel details
Collapse hotel details
Reviewed 6 days ago

My friend and I did a Mom's weekend getaway at the Garden Gables Inn. The rooms were lovely. Beds were super comfortable. We had massages in their spa room, which were incredibly relaxing...More

Reviewed 1 week ago

My wife and I stayed one night here in the Berkshires and really wished for more. This a beautiful B&B with pleasant grounds and a huge swimming pool (closed for the season). We stayed in the...More

Hotel website
135 Main St, Lenox, MA 01240-2396
(413) 207-9493
Pool
Free Parking
Free Wifi
Breakfast included
4.0 Star Hotel
Renaissance Albany Hotel
Renaissance Hotels
US$ 204
View Deal
80.3 km from Chesterfield
  • Free Wifi
  • Restaurant
Special offer
Special OfferEarn a Free Night
View hotel details
Collapse hotel details
Reviewed 2 days ago

All the staff were extremely kind and helpful especially the staff in the restaurant. The parking garage was very convenient to the hotel and priced well for being a downtown garage. Hotel was...More

Reviewed 1 week ago

This is the third time we have stayed at the Renaissance and I LOVE IT. The hotel is gorgeous...perched on the edge of the Empire State Plaza with the quirky lobby stuffed with gorgeous murals and...More

Hotel website
144 State St, Albany, NY 12207-1605
Room Service
Restaurant
Bar/Lounge
Free Wifi
Fitness centre
3.5 Star Hotel
Black Swan Inn Berkshires, an Ascend Collection Hotel
SAVE US$ 3
US$ 109
AscendHotels
US$ 106
View Deal