Top Rated Resorts in Chesterfield
The Common Man Inn & Restaurant
- Restaurant
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Garden area
The Common Man Inn & Restaurant
- Restaurant
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Garden area
The Common Man Inn & Restaurant
D. Hotel Suites & Spa
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Sauna
- Heated swimming pool
Featuring a lift and a vending machine, the 3-star D. Hotel Suites & Spa Holyoke sits in Holyoke. This Holyoke hotel provides Wi-Fi throughout the property.
Options for an active stay feature a fitness centre and a heated pool available on site.
D. Hotel Suites & Spa
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Sauna
- Heated swimming pool
D. Hotel Suites & Spa
Featuring a lift and a vending machine, the 3-star D. Hotel Suites & Spa Holyoke sits in Holyoke. This Holyoke hotel provides Wi-Fi throughout the property.
Options for an active stay feature a fitness centre and a heated pool available on site.
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Guest favorite
Vacation Village In The Berkshires
- BBQ facilities
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Pool with view
Located within 25 minutes' walk of Brodie Mountain, the 5-star smoke-free Vacation Village In The Berkshires Hancock hotel includes a sunbathing terrace, a patio, and a picnic area.
A swimming pool is provided onsite the Vacation Village. An array of activities is offered in the area, such as biking, downhill skiing, and billiard.
Vacation Village In The Berkshires
- BBQ facilities
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Pool with view
Vacation Village In The Berkshires
Located within 25 minutes' walk of Brodie Mountain, the 5-star smoke-free Vacation Village In The Berkshires Hancock hotel includes a sunbathing terrace, a patio, and a picnic area.
A swimming pool is provided onsite the Vacation Village. An array of activities is offered in the area, such as biking, downhill skiing, and billiard.
Budget Resorts in Chesterfield
-
Best-rated
Vikings Villages Resort
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Terrace
There is also private parking.
This Guilford resort provides boating, hiking, and skiing for an active pastime.
Vikings Villages Resort
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Terrace
Vikings Villages Resort
There is also private parking.
This Guilford resort provides boating, hiking, and skiing for an active pastime.
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Top location
Holiday Inn Express Hotel & Suites Brattleboro By Ihg
- Free parking
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Fitness centre
- Heated swimming pool
Holiday Inn Express Hotel & Suites Brattleboro By Ihg, located 6 km from Fair Winds Farm, boasts a heated pool. This hotel has 86 rooms and features a lift and a vending machine on-site.
A 24-hour fitness center, along with fitness classes, is included at the Holiday Inn Express to help guests maintain their physical well-being.
Holiday Inn Express Hotel & Suites Brattleboro By Ihg
- Free parking
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Fitness centre
- Heated swimming pool
Holiday Inn Express Hotel & Suites Brattleboro By Ihg
Holiday Inn Express Hotel & Suites Brattleboro By Ihg, located 6 km from Fair Winds Farm, boasts a heated pool. This hotel has 86 rooms and features a lift and a vending machine on-site.
A 24-hour fitness center, along with fitness classes, is included at the Holiday Inn Express to help guests maintain their physical well-being.
Club Wyndham Bentley Brook
- BBQ facilities
- Free parking
- Air conditioning
- Laundry
- Sauna
- Outdoor swimming pool
Club Wyndham Bentley Brook Hotel Hancock offers 152 rooms and an adult pool with a hot tub. Situated right by ski slopes and a ski mountain, this hotel provides guests with ski equipment hire.
The Bentley Brook spoils guests with a Jacuzzi and a sauna along with such activities as snow skiing, hiking, and billiard. Guests can work out in a hotel fitness centre during their stay.
Club Wyndham Bentley Brook
- BBQ facilities
- Free parking
- Air conditioning
- Laundry
- Sauna
- Outdoor swimming pool
Club Wyndham Bentley Brook
Club Wyndham Bentley Brook Hotel Hancock offers 152 rooms and an adult pool with a hot tub. Situated right by ski slopes and a ski mountain, this hotel provides guests with ski equipment hire.
The Bentley Brook spoils guests with a Jacuzzi and a sauna along with such activities as snow skiing, hiking, and billiard. Guests can work out in a hotel fitness centre during their stay.
Resorts in Chesterfield for Couples
Hotel Downstreet, An Ascend Collection Hotel
- Restaurant
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Indoor swimming pool
Located merely 14 minutes' stroll from All Saints Episcopal Church, the 4-star smoke-free Hotel Downstreet, An Ascend Collection Hotel North Adams boasts a Jacuzzi and a sauna.
Such leisure options as a swimming pool, a fitness centre will ensure a more relaxing stay. The accommodation offers skiing and ping pong for guests to practise sports.
Hotel Downstreet, An Ascend Collection Hotel
- Restaurant
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Indoor swimming pool
Hotel Downstreet, An Ascend Collection Hotel
Located merely 14 minutes' stroll from All Saints Episcopal Church, the 4-star smoke-free Hotel Downstreet, An Ascend Collection Hotel North Adams boasts a Jacuzzi and a sauna.
Such leisure options as a swimming pool, a fitness centre will ensure a more relaxing stay. The accommodation offers skiing and ping pong for guests to practise sports.
Colonial Hotel
- Restaurant
- Free parking
- 24-hour reception
- Air conditioning
- Sauna
- Indoor swimming pool
Located 25 minutes' walk from the American Dunn State Public Park, which offers the thrill of discovering something beautiful, Colonial Hotel Gardner offers a restaurant.
An indoor pool comes with a hot tub.
Colonial Hotel
- Restaurant
- Free parking
- 24-hour reception
- Air conditioning
- Sauna
- Indoor swimming pool
Colonial Hotel
Located 25 minutes' walk from the American Dunn State Public Park, which offers the thrill of discovering something beautiful, Colonial Hotel Gardner offers a restaurant.
An indoor pool comes with a hot tub.
Best Western Springfield Hotel
- Free parking
- 24-hour reception
- Air conditioning
- Leisure/ TV room
- Fitness centre
- Indoor swimming pool
Nestled in a business area of Springfield, the comfortable 3-star Best Western Springfield Hotel offers air-conditioned rooms.
A shared lounge and a golf course are provided for a truly enjoyable stay. Guests can join canyoning, hiking, and billiard.
Best Western Springfield Hotel
- Free parking
- 24-hour reception
- Air conditioning
- Leisure/ TV room
- Fitness centre
- Indoor swimming pool
Best Western Springfield Hotel
Nestled in a business area of Springfield, the comfortable 3-star Best Western Springfield Hotel offers air-conditioned rooms.
A shared lounge and a golf course are provided for a truly enjoyable stay. Guests can join canyoning, hiking, and billiard.
Party Resorts in Chesterfield
The Hotel Northampton
- Restaurant
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Terrace
The comfortable The Hotel Northampton enjoys a central location and provides easy access to Smith College Museum of Art only 9 minutes' walk away. The highlights of this 3-star hotel include a vending machine and a lift, it also offers Wi-Fi in public areas.
The Hotel Northampton
- Restaurant
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Terrace
The Hotel Northampton
The comfortable The Hotel Northampton enjoys a central location and provides easy access to Smith College Museum of Art only 9 minutes' walk away. The highlights of this 3-star hotel include a vending machine and a lift, it also offers Wi-Fi in public areas.
The Williams Inn
- Restaurant
- Free parking
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Live entertainment
The 4-star designer The Williams Inn Williamstown offers quick access to The Soldiers' Monument, located a mere 6 minutes' walk away.
A shared lounge and a golf course are also featured at this Williamstown hotel.
The Williams Inn
- Restaurant
- Free parking
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Live entertainment
The Williams Inn
The 4-star designer The Williams Inn Williamstown offers quick access to The Soldiers' Monument, located a mere 6 minutes' walk away.
A shared lounge and a golf course are also featured at this Williamstown hotel.
The Upper Pass Lodge
- Restaurant
- Free parking
- VIP check-in/ -out
- Air conditioning
- Skiing
- Outdoor swimming pool
A car park is provided on site.
Guests will take advantage of hiking, skiing, and cycling available for an active pastime.
The Upper Pass Lodge
- Restaurant
- Free parking
- VIP check-in/ -out
- Air conditioning
- Skiing
- Outdoor swimming pool
The Upper Pass Lodge
A car park is provided on site.
Guests will take advantage of hiking, skiing, and cycling available for an active pastime.
Golf Resorts in Chesterfield
Chalet 239-Boutique Hotel
- Picnic area/ Tables
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Patio
Situated a stone's throw from Sports Oddyssey Ski Shop, the comfortable Chalet 239-Boutique Hotel West Dover offers proximity to various city highlights.
Chalet 239-Boutique Hotel
- Picnic area/ Tables
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Patio
Chalet 239-Boutique Hotel
Situated a stone's throw from Sports Oddyssey Ski Shop, the comfortable Chalet 239-Boutique Hotel West Dover offers proximity to various city highlights.
Holiday Inn Club Vacations Mount Ascutney Resort
- BBQ facilities
- Free parking
- Express check-in/ -out
- Air conditioning
- Live entertainment
- Outdoor swimming pool
The 4-star Holiday Inn Club Vacations Mount Ascutney Resort Brownsville provides proximity to American Precision Museum, which is located around 7 km away.
Staying at the Holiday Inn Brownsville, guests can dive in an indoor pool. The area is known for hiking, basketball, and ping pong.
Holiday Inn Club Vacations Mount Ascutney Resort
- BBQ facilities
- Free parking
- Express check-in/ -out
- Air conditioning
- Live entertainment
- Outdoor swimming pool
Holiday Inn Club Vacations Mount Ascutney Resort
The 4-star Holiday Inn Club Vacations Mount Ascutney Resort Brownsville provides proximity to American Precision Museum, which is located around 7 km away.
Staying at the Holiday Inn Brownsville, guests can dive in an indoor pool. The area is known for hiking, basketball, and ping pong.
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Great deal
Red Roof Inn Plus+ South Deerfield - Amherst
- Free parking
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Laundry
- Sun loungers
Offering an indoor pool and a game area, the 3-star Red Roof Inn Plus+ South Deerfield - Amherst is 2.7 km from the butte-like Sugarloaf Mountain. The hotel offers Wi-Fi in public areas as well as cash machine/banking services and a 24-hour front desk.
Red Roof Inn Plus+ South Deerfield - Amherst
- Free parking
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Laundry
- Sun loungers
Red Roof Inn Plus+ South Deerfield - Amherst
Offering an indoor pool and a game area, the 3-star Red Roof Inn Plus+ South Deerfield - Amherst is 2.7 km from the butte-like Sugarloaf Mountain. The hotel offers Wi-Fi in public areas as well as cash machine/banking services and a 24-hour front desk.
Honeymoon Resorts in Chesterfield
210 Cedarbrook Queen Studio
- Cookware/ Kitchen utensils
- Tours/Ticket assistance
- Flat-screen TV
- Heating
- Fitness centre
- Heated swimming pool
The comfortable 210 Cedarbrook Queen Studio Killington hotel includes air-conditioned rooms and is located approximately 10 minutes by car from Snowdon Quad.
Other facilities include an outdoor swimming pool.
210 Cedarbrook Queen Studio
- Cookware/ Kitchen utensils
- Tours/Ticket assistance
- Flat-screen TV
- Heating
- Fitness centre
- Heated swimming pool
210 Cedarbrook Queen Studio
The comfortable 210 Cedarbrook Queen Studio Killington hotel includes air-conditioned rooms and is located approximately 10 minutes by car from Snowdon Quad.
Other facilities include an outdoor swimming pool.
Jiminy Peak Mountain Resort
- BBQ facilities
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Heated swimming pool
Positioned 1.4 km from Ioka Valley Farm and about 10 minutes' drive from Ramblewild Adventure Park Recreation Center, the 3-star Jiminy Peak Mountain Resort Hancock presents 2 outdoor tennis courts. Featuring a restaurant, the resort is located a few steps from Jiminy Peak Mountain Resort.
You can spend time by a heated pool, which comes with a hot tub. Guests staying at this accommodation are welcome to join fitness classes at a fitness centre.
Jiminy Peak Mountain Resort
- BBQ facilities
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Heated swimming pool
Jiminy Peak Mountain Resort
Positioned 1.4 km from Ioka Valley Farm and about 10 minutes' drive from Ramblewild Adventure Park Recreation Center, the 3-star Jiminy Peak Mountain Resort Hancock presents 2 outdoor tennis courts. Featuring a restaurant, the resort is located a few steps from Jiminy Peak Mountain Resort.
You can spend time by a heated pool, which comes with a hot tub. Guests staying at this accommodation are welcome to join fitness classes at a fitness centre.
Holiday Inn & Suites Pittsfield-Berkshires By Ihg
- Restaurant
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Live entertainment
- Heated swimming pool
Featuring a sun deck, spa therapy, and a golf course, the 4-star Holiday Inn & Suites Pittsfield-Berkshires By Ihg enjoys a convenient location 17 minutes' walk from Pittsfield Mall. Boasting a swimming pool along with an American restaurant, the hotel is located a few steps from the Your Berkshire Community Museum.
Holiday Inn & Suites Pittsfield-Berkshires By Ihg
- Restaurant
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Live entertainment
- Heated swimming pool
Holiday Inn & Suites Pittsfield-Berkshires By Ihg
Featuring a sun deck, spa therapy, and a golf course, the 4-star Holiday Inn & Suites Pittsfield-Berkshires By Ihg enjoys a convenient location 17 minutes' walk from Pittsfield Mall. Boasting a swimming pool along with an American restaurant, the hotel is located a few steps from the Your Berkshire Community Museum.
4 Star Resorts in Chesterfield
The Pointe At Castle Hill Resort & Spa
- Free parking
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Fitness centre
- Indoor swimming pool
Offering a shared lounge and a golf course, the smoke-free The Pointe At Castle Hill Resort & Spa Proctorsville lies in a rural area of Proctorsville, approximately 6 km from Jackson Gore Ski Area and within a 10-minute drive of Congregational Church of Ludlow. This 3-star resort features a swimming pool, a fitness centre and high-speed Internet access in public areas.
After a busy day you can recover in a solarium, a Jacuzzi, and a sauna or indulge in a hot stone massage, a sports massage, and a prenatal massage. Activities such as hiking, skiing, and billiard can be arranged by this Proctorsville hotel. The Pointe also features conference facilities and complimentary wireless internet access for those arriving on business.
The Pointe At Castle Hill Resort & Spa
- Free parking
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Fitness centre
- Indoor swimming pool
The Pointe At Castle Hill Resort & Spa
Offering a shared lounge and a golf course, the smoke-free The Pointe At Castle Hill Resort & Spa Proctorsville lies in a rural area of Proctorsville, approximately 6 km from Jackson Gore Ski Area and within a 10-minute drive of Congregational Church of Ludlow. This 3-star resort features a swimming pool, a fitness centre and high-speed Internet access in public areas.
After a busy day you can recover in a solarium, a Jacuzzi, and a sauna or indulge in a hot stone massage, a sports massage, and a prenatal massage. Activities such as hiking, skiing, and billiard can be arranged by this Proctorsville hotel. The Pointe also features conference facilities and complimentary wireless internet access for those arriving on business.
Are you in a hurry?
Here is a quick list of Resorts in Chesterfield, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| The Common Man Inn & Restaurant |
9.3 / 10 (365 Reviews) |
From 119$ | |
| D. Hotel Suites & Spa |
8.8 / 10 (1005 Reviews) |
From 122$ | |
| Vacation Village In The Berkshires |
8.6 / 10 (1287 Reviews) |
From 135$ | |
| Vikings Villages Resort |
9.8 / 10 (449 Reviews) |
From 287$ | |
| Holiday Inn Express Hotel & Suites Brattleboro By Ihg |
8.7 / 10 (161 Reviews) |
From 100$ |