Hotels in Chesterfield
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Aug 12 - Aug 13Tomorrow
Aug 13 - Aug 14This weekend
Aug 14 - Aug 16Next weekend
Aug 21 - Aug 23Top 5 hotels in Chesterfield at a glance
- 1. Hampton Inn Brattleboro — 2.5-star hotel in Brattleboro. Guest rating: 8.2/10 — Very Good.
- 2. Comfort Inn & Suites Brattleboro I-91 — 2.5-star hotel in Brattleboro. Guest rating: 8.6/10 — Excellent.
- 3. Riverside Hotel, an Ascend Collection Hotel — 2.5-star hotel in West Chesterfield. Guest rating: 9.6/10 — Exceptional.
- 4. Holiday Inn Express Hotel & Suites Brattleboro by IHG — 2.5-star hotel in Brattleboro. Guest rating: 9.0/10 — Wonderful.
- 5. Colonial Motel — 3-star hotel in Brattleboro. Guest rating: 6.8/10.
Where to stay in Chesterfield?




1. Hampton Inn Brattleboro
Hampton Inn BrattleboroBrattleboro
$118
$130 total
includes taxes & fees
Sep 8 - Sep 9




2. Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91Brattleboro
$135
$149 total
includes taxes & fees
Sep 6 - Sep 7




3. Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection HotelWest Chesterfield
$152
$165 total
includes taxes & fees
Sep 10 - Sep 11




4. Holiday Inn Express Hotel & Suites Brattleboro by IHG
Holiday Inn Express Hotel & Suites Brattleboro by IHGBrattleboro
$173
$190 total
includes taxes & fees
Sep 6 - Sep 7




5. Colonial Motel
Colonial MotelBrattleboro
$77
$84 total
includes taxes & fees
Aug 13 - Aug 14




6. Latchis Hotel
Latchis HotelBrattleboro
$121
$133 total
includes taxes & fees
Aug 23 - Aug 24




7. Travelodge by Wyndham Brattleboro VT
Travelodge by Wyndham Brattleboro VTBrattleboro
$65
$71 total
includes taxes & fees
Aug 30 - Aug 31




8. Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection HotelKeene
$120
$130 total
includes taxes & fees
Sep 1 - Sep 2




9. Black Mountain Inn
Black Mountain InnBrattleboro
$139
$153 total
includes taxes & fees
Aug 13 - Aug 14




10. The Covered Bridge Inn
The Covered Bridge InnBrattleboro
$115
$127 total
includes taxes & fees
Aug 26 - Aug 27




11. The Putney Inn
The Putney InnPutney
$138
$151 total
includes taxes & fees
Aug 13 - Aug 14




12. Days Inn by Wyndham Keene NH
Days Inn by Wyndham Keene NHKeene
$93
$101 total
includes taxes & fees
Aug 23 - Aug 24




13. Best Western Plus Keene Hotel
Best Western Plus Keene HotelKeene
$149
$162 total
includes taxes & fees
Aug 19 - Aug 20




14. Hampton Inn & Suites Keene
Hampton Inn & Suites KeeneKeene
$147
$159 total
includes taxes & fees
Aug 30 - Aug 31




15. The Burrell House
The Burrell HouseKeene
$122
$136 total
includes taxes & fees
Aug 17 - Aug 18




16. Econo Lodge Brattleboro South
Econo Lodge Brattleboro SouthBrattleboro
$89
$98 total
includes taxes & fees
Aug 19 - Aug 20




17. Chesterfield Inn
Chesterfield InnWest Chesterfield
$301
$327 total
includes taxes & fees
Aug 13 - Aug 14




18. Fairfield Inn & Suites by Marriott Keene Downtown
Fairfield Inn & Suites by Marriott Keene DowntownKeene
$161
$174 total
includes taxes & fees
Aug 26 - Aug 27




19. Vikings Villages Resort
Vikings Villages ResortGuilford
$170
$199 total
includes taxes & fees
Sep 8 - Sep 9




20. Windmill Motel Restaurant
Windmill Motel RestaurantBernardston
$122
$136 total
includes taxes & fees
Aug 13 - Aug 14
Go beyond your typical stay in Chesterfield
Pet friendly
Apartment
Cottage
Family friendly
Top landmarks in Chesterfield
Asbury United Methodist Church
If you're planning a bit of sightseeing during your trip, head to Asbury United Methodist Church— just one of the monuments in central Chesterfield.
Chesterfield Town Hall
Chesterfield Town Hall is worth a visit when in central Chesterfield.
Learn more about Chesterfield
Chesterfield is well-known for its attractions such as Asbury United Methodist Church and Pisgah State Park.
See all hotels in Chesterfield
Check out reviews of Chesterfield hotels guests love
Hampton Inn Brattleboro
10/10 Excellent
"Lovely Hampton. Great staff. Would recommend."
Keene Elm City Hotel, an Ascend Collection Hotel
10/10 Excellent
"Everything was very clean and very well taken care of. The bed was very comfortable the place where I think maybe the stay was lacking was the breakfast, not very exciting. It was adequate and well stocked. I do like that. There was coffee available 24 hours."
Vikings Villages Resort
10/10 Excellent
"We went just for a quiet night away and it surpassed my expectations. The cabins were wonderful and there was plenty to do to keep my teenagers entertained."
Riverside Hotel, an Ascend Collection Hotel
10/10 Excellent
"Balcony over looking the river. Very relaxing"
The Inn At Crumpin Fox
8/10 Good
"This hotel is a solid option when exploring the northern edges of Western Mass. The air conditioning was fantastic, and in an area where many have none, or are working from window units, this was useful for an August stay. There are no real frills at The Inn, but the water pressure is good and the AC works, so that’s a high recommendation."
Windmill Motel Restaurant
10/10 Excellent
"I love the outdoor seating area with the tent and outdoor couches and I love the colors and textures used for the room I stayed in. When I checked in, I was hot from being at SoulFest and the owners gave me a cloth hand fan for free! When I came home that night, I was hungry and there were chips and chocolates in my room! That was wonderful and thoughtful. They also sell food in the office, if you need something more substantial. The mattress and pillows were so comfortable that I had trouble getting myself up the next morning! Slept like a rock. 10/10 for the Windmill! Can't wait to see what the restaurant will be like when it opens! I will definitely come back next year, if there is availability!"
Latchis Hotel
8/10 Good
"In an old Theater building. Definitely has character and cool features. We arrived too late for the movies, but still fun. In central Brattleboro which has some interesting shops, but is suffering from homelessnes and mental illness/drug use. Didnt really feel unsafe and we walked a few blocks to a fun restaurant with good food & karioke. Person at desk was lovely and helpful. Room was ok- a little dated and could be cleaner."
The Putney Inn
8/10 Good
"I feel the 8.6 is much too overrated. A 7, maybe. Old building, needs a facelift. Clean, but does not feel as a happy place. Old rugs. Very dark ( but clean) rooms. Felt like in a cave. Manager had no people skills, not welcoming. Will not stay there again. Put a little money into the place!"
Fairfield Inn & Suites by Marriott Keene Downtown
8/10 Good
"Just one point the air conditioning was either too hot or too cold."
