Resort Getaways Chesterfield
Chesterfield
2 guests

Adults:

2

Children:

0

Child’s age:

Chesterfield

Nov 06 - Nov 07 ·
2 guests

Chesterfield Resorts

Chesterfield
2 guests

Adults:

2

Children:

0

Child’s age:

Navigation

1. The Common Man Inn & Restaurant

2. D. Hotel Suites & Spa

3. Vacation Village In The Berkshires

4. Vikings Villages Resort

Budget Resorts in Chesterfield

5. Holiday Inn Express Hotel & Suites Brattleboro By Ihg

6. Club Wyndham Bentley Brook

7. Hotel Downstreet, An Ascend Collection Hotel

Resorts in Chesterfield for Couples

8. Best Western Springfield Hotel

9. The Hotel Northampton

10. The Upper Pass Lodge

Top Rated Resorts in Chesterfield

Resorts near Chesterfield

The Common Man Inn & Restaurant The Common Man Inn & Restaurant

The Common Man Inn & Restaurant

21 Water St
54.2 km (33.7 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Garden area
9.3
365 reviews
~ US$119 / night

The Common Man Inn & Restaurant

54.2 km (33.7 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Garden area

The Common Man Inn & Restaurant

9.3
365 reviews
From US$ 119 / night
D. Hotel Suites & Spa D. Hotel Suites & Spa

D. Hotel Suites & Spa

1 Country Club Road
70.6 km (43.9 mi) from Chesterfield
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Sauna
  • Heated swimming pool
8.8
1003 reviews
~ US$122 / night

D. Hotel Suites & Spa

70.6 km (43.9 mi) from Chesterfield
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Sauna
  • Heated swimming pool

D. Hotel Suites & Spa

8.8
1003 reviews
From US$ 122 / night
  • Guest favorite
Vacation Village In The Berkshires Vacation Village In The Berkshires

Vacation Village In The Berkshires

276 Brodie Mountain Road
73.7 km (45.8 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Pool with view

Featuring Wi-Fi in public areas, the smoke-free Vacation Village In The Berkshires Hancock hotel sits around 10 minutes' drive from Ioka Valley Farm. To keep the little ones entertained, the 5-star resort provides offerings like board games and kids' outdoor play equipment.

Boasting a heated pool, this Hancock hotel also provides a sun deck and a patio. The accommodation features biking, hiking, and billiard for sport lovers.

8.6
1287 reviews
~ US$135 / night

Vacation Village In The Berkshires

73.7 km (45.8 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Pool with view

Vacation Village In The Berkshires

Featuring Wi-Fi in public areas, the smoke-free Vacation Village In The Berkshires Hancock hotel sits around 10 minutes' drive from Ioka Valley Farm. To keep the little ones entertained, the 5-star resort provides offerings like board games and kids' outdoor play equipment.

Boasting a heated pool, this Hancock hotel also provides a sun deck and a patio. The accommodation features biking, hiking, and billiard for sport lovers.

8.6
1287 reviews
From US$ 135 / night

Budget Resorts in Chesterfield

  • Best-rated
Vikings Villages Resort Vikings Villages Resort

Vikings Villages Resort

360 Vikings Village Dr
15.6 km (9.7 mi) from Chesterfield
63
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Terrace

Guests of the comfortable Vikings Villages Resort Guilford can enjoy access to Christ Church, located nearly 10 minutes' drive away. Private parking is available on site at the smoke-free hotel.

You can also enjoy boating, hiking, and skiing at the Vikings Guilford.

9.8
447 reviews
~ US$287 / night

Vikings Villages Resort

15.6 km (9.7 mi) from Chesterfield
63
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Terrace

Vikings Villages Resort

Guests of the comfortable Vikings Villages Resort Guilford can enjoy access to Christ Church, located nearly 10 minutes' drive away. Private parking is available on site at the smoke-free hotel.

You can also enjoy boating, hiking, and skiing at the Vikings Guilford.

9.8
447 reviews
From US$ 287 / night
  • Top location
Holiday Inn Express Hotel & Suites Brattleboro By Ihg Holiday Inn Express Hotel & Suites Brattleboro By Ihg

Holiday Inn Express Hotel & Suites Brattleboro By Ihg

100 Chickering Drive
4.8 km (3.0 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Fitness centre
  • Heated swimming pool

The 2-star Holiday Inn Express Hotel & Suites Brattleboro By Ihg is approximately a 10-minute ride from Connecticut River and provides guests with a lift and a vending machine. Boasting a location within reach of Saxtons Distillery, this Brattleboro hotel features 86 rooms as well as luggage storage.

Holiday Inn Express Hotel & Suites Brattleboro By Ihg also includes an indoor pool and a 24-hour fitness center.

8.7
161 reviews
~ US$100 / night

Holiday Inn Express Hotel & Suites Brattleboro By Ihg

4.8 km (3.0 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Fitness centre
  • Heated swimming pool

Holiday Inn Express Hotel & Suites Brattleboro By Ihg

The 2-star Holiday Inn Express Hotel & Suites Brattleboro By Ihg is approximately a 10-minute ride from Connecticut River and provides guests with a lift and a vending machine. Boasting a location within reach of Saxtons Distillery, this Brattleboro hotel features 86 rooms as well as luggage storage.

Holiday Inn Express Hotel & Suites Brattleboro By Ihg also includes an indoor pool and a 24-hour fitness center.

8.7
161 reviews
From US$ 100 / night
Club Wyndham Bentley Brook Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

1 Corey Road
74.3 km (46.2 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Laundry
  • Sauna
  • Outdoor swimming pool

Wi-Fi is available in the rooms for both business and leisure purposes.

The Bentley Brook Hancock houses a Jacuzzi and a sauna on site. On the premises, a heated pool, a hotel fitness centre as well as opportunities for snow skiing, hiking, and billiard are provided.

9.1
287 reviews
~ US$167 / night

Club Wyndham Bentley Brook

74.3 km (46.2 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Laundry
  • Sauna
  • Outdoor swimming pool

Club Wyndham Bentley Brook

Wi-Fi is available in the rooms for both business and leisure purposes.

The Bentley Brook Hancock houses a Jacuzzi and a sauna on site. On the premises, a heated pool, a hotel fitness centre as well as opportunities for snow skiing, hiking, and billiard are provided.

9.1
287 reviews
From US$ 167 / night

Resorts in Chesterfield for Couples

Hotel Downstreet, An Ascend Collection Hotel Hotel Downstreet, An Ascend Collection Hotel

Hotel Downstreet, An Ascend Collection Hotel

40 Main Street
53.8 km (33.5 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Indoor swimming pool

The 4-star smoke-free Hotel Downstreet, An Ascend Collection Hotel North Adams provides proximity to All Saints Episcopal Church, which is located just 1.1 km away. You can swim in a swimming pool or take advantage of a Jacuzzi and a sauna at this North Adams hotel.

Guests can make use of skiing and table tennis, along with cars for rent. At Hotel Downstreet, An Ascend Collection Hotel, guests can take part in fitness classes offered at a fitness suite.

8.5
208 reviews
~ US$108 / night

Hotel Downstreet, An Ascend Collection Hotel

53.8 km (33.5 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Indoor swimming pool

Hotel Downstreet, An Ascend Collection Hotel

The 4-star smoke-free Hotel Downstreet, An Ascend Collection Hotel North Adams provides proximity to All Saints Episcopal Church, which is located just 1.1 km away. You can swim in a swimming pool or take advantage of a Jacuzzi and a sauna at this North Adams hotel.

Guests can make use of skiing and table tennis, along with cars for rent. At Hotel Downstreet, An Ascend Collection Hotel, guests can take part in fitness classes offered at a fitness suite.

8.5
208 reviews
From US$ 108 / night
Best Western Springfield Hotel Best Western Springfield Hotel

Best Western Springfield Hotel

818 Charlestown Road
40.7 km (25.3 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Leisure/ TV room
  • Fitness centre
  • Indoor swimming pool

The affordable Best Western Springfield Hotel offers parking nearby.

Leisure options include a shared lounge and a golf course.

8.9
214 reviews
~ US$164 / night

Best Western Springfield Hotel

40.7 km (25.3 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Leisure/ TV room
  • Fitness centre
  • Indoor swimming pool

Best Western Springfield Hotel

The affordable Best Western Springfield Hotel offers parking nearby.

Leisure options include a shared lounge and a golf course.

8.9
214 reviews
From US$ 164 / night
The Hotel Northampton The Hotel Northampton

The Hotel Northampton

36 King Street
65.6 km (40.8 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Terrace

Located a mere 7 minutes' walk from Pulaski Park, the comfortable The Hotel Northampton offers modern comforts such as a lift and a vending machine. This 3-star hotel features 89 rooms and such amenities as a restaurant and luggage storage.

8.7
398 reviews
~ US$186 / night

The Hotel Northampton

65.6 km (40.8 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Terrace

The Hotel Northampton

Located a mere 7 minutes' walk from Pulaski Park, the comfortable The Hotel Northampton offers modern comforts such as a lift and a vending machine. This 3-star hotel features 89 rooms and such amenities as a restaurant and luggage storage.

8.7
398 reviews
From US$ 186 / night

Party Resorts in Chesterfield

The Upper Pass Lodge The Upper Pass Lodge

The Upper Pass Lodge

420 Magic Mountain Access Road
39.3 km (24.4 mi) from Chesterfield
  • Restaurant
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Skiing
  • Outdoor swimming pool

Providing 21 rooms, the comfortable 2-star The Upper Pass Lodge Londonderry hotel is approximately a 10-minute ride from Viking Nordic Center Ski Club. Featuring luggage storage and a restaurant, this Londonderry hotel is located in the immediate vicinity of Magic Mountain Ski Area.

This Londonderry hotel invites guests to spend time by a seasonal outdoor swimming pool. The property is a perfect place to practise hiking, skiing, and cycling.

8.2
149 reviews
~ US$103 / night

The Upper Pass Lodge

39.3 km (24.4 mi) from Chesterfield
  • Restaurant
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Skiing
  • Outdoor swimming pool

The Upper Pass Lodge

Providing 21 rooms, the comfortable 2-star The Upper Pass Lodge Londonderry hotel is approximately a 10-minute ride from Viking Nordic Center Ski Club. Featuring luggage storage and a restaurant, this Londonderry hotel is located in the immediate vicinity of Magic Mountain Ski Area.

This Londonderry hotel invites guests to spend time by a seasonal outdoor swimming pool. The property is a perfect place to practise hiking, skiing, and cycling.

8.2
149 reviews
From US$ 103 / night
Colonial Hotel Colonial Hotel

Colonial Hotel

625 Betty Spring Road
59.7 km (37.1 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Sauna
  • Indoor swimming pool

The 3-star smoke-free Colonial Hotel Gardner is located around a 15-minute ride from Faith Lutheran Church and has a swimming pool with a hot tub.

This Gardner hotel offers such treatments as a Jacuzzi and a sauna. There is a fitness centre at the accommodation.

8
402 reviews
~ US$130 / night

Colonial Hotel

59.7 km (37.1 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Sauna
  • Indoor swimming pool

Colonial Hotel

The 3-star smoke-free Colonial Hotel Gardner is located around a 15-minute ride from Faith Lutheran Church and has a swimming pool with a hot tub.

This Gardner hotel offers such treatments as a Jacuzzi and a sauna. There is a fitness centre at the accommodation.

8
402 reviews
From US$ 130 / night
The Williams Inn The Williams Inn

The Williams Inn

101 Spring Street
60.2 km (37.4 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Live entertainment

The smoke-free The Williams Inn Williamstown is situated in the very heart of Williamstown and features Wi-Fi in public areas.

A shared lounge and a golf course are also provided on site for your pleasure.

9.4
152 reviews
~ US$246 / night

The Williams Inn

60.2 km (37.4 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Live entertainment

The Williams Inn

The smoke-free The Williams Inn Williamstown is situated in the very heart of Williamstown and features Wi-Fi in public areas.

A shared lounge and a golf course are also provided on site for your pleasure.

9.4
152 reviews
From US$ 246 / night

Golf Resorts in Chesterfield

Holiday Inn Club Vacations Mount Ascutney Resort Holiday Inn Club Vacations Mount Ascutney Resort

Holiday Inn Club Vacations Mount Ascutney Resort

485 Hotel Road
62.6 km (38.9 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Live entertainment
  • Outdoor swimming pool

Located 2.8 km from such natural attractions as the scenic mountain "Mount Ascutney", the 4-star Holiday Inn Club Vacations Mount Ascutney Resort Brownsville includes a restaurant.

A swimming pool is provided onsite this Brownsville hotel. Lawn tennis, basketball, and billiard may be organised by the property for guests.

8.9
216 reviews
~ US$231 / night

Holiday Inn Club Vacations Mount Ascutney Resort

62.6 km (38.9 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Live entertainment
  • Outdoor swimming pool

Holiday Inn Club Vacations Mount Ascutney Resort

Located 2.8 km from such natural attractions as the scenic mountain "Mount Ascutney", the 4-star Holiday Inn Club Vacations Mount Ascutney Resort Brownsville includes a restaurant.

A swimming pool is provided onsite this Brownsville hotel. Lawn tennis, basketball, and billiard may be organised by the property for guests.

8.9
216 reviews
From US$ 231 / night
Chalet 239-Boutique Hotel Chalet 239-Boutique Hotel

Chalet 239-Boutique Hotel

239 Vermont Route 100
29.3 km (18.2 mi) from Chesterfield
  • Picnic area/ Tables
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Patio

The comfortable Chalet 239-Boutique Hotel West Dover offers quick access to "Memorial Hall Center for the Arts, situated nearly 5 minutes' walk away.

8.9
189 reviews
~ US$234 / night

Chalet 239-Boutique Hotel

29.3 km (18.2 mi) from Chesterfield
  • Picnic area/ Tables
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Patio

Chalet 239-Boutique Hotel

The comfortable Chalet 239-Boutique Hotel West Dover offers quick access to "Memorial Hall Center for the Arts, situated nearly 5 minutes' walk away.

8.9
189 reviews
From US$ 234 / night
  • Great deal
Red Roof Inn Plus+ South Deerfield - Amherst Red Roof Inn Plus+ South Deerfield - Amherst

Red Roof Inn Plus+ South Deerfield - Amherst

9 Greenfield Road
48.7 km (30.3 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Laundry
  • Sun loungers

An indoor swimming pool and a game area are available at Red Roof Inn Plus+ South Deerfield - Amherst, and Buttonball Tree is 3.1 km away. With Wi-Fi in public areas, the hotel offers cash machine/banking services and a 24-hour front desk.

6.5
418 reviews
~ US$67 / night

Red Roof Inn Plus+ South Deerfield - Amherst

48.7 km (30.3 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Laundry
  • Sun loungers

Red Roof Inn Plus+ South Deerfield - Amherst

An indoor swimming pool and a game area are available at Red Roof Inn Plus+ South Deerfield - Amherst, and Buttonball Tree is 3.1 km away. With Wi-Fi in public areas, the hotel offers cash machine/banking services and a 24-hour front desk.

6.5
418 reviews
From US$ 67 / night

Honeymoon Resorts in Chesterfield

210 Cedarbrook Queen Studio 210 Cedarbrook Queen Studio

210 Cedarbrook Queen Studio

8463 Us Route 4
79.8 km (49.6 mi) from Chesterfield
  • 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 3.4 km from Northbrook Quad.

This accommodation also has an outdoor swimming pool.

9.3
31 reviews
~ US$179 / night

210 Cedarbrook Queen Studio

79.8 km (49.6 mi) from Chesterfield
  • 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 3.4 km from Northbrook Quad.

This accommodation also has an outdoor swimming pool.

9.3
31 reviews
From US$ 179 / night
Jiminy Peak Mountain Resort Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

37 Corey Road
74.5 km (46.3 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Heated swimming pool

Jiminy Peak Mountain Resort Hancock, located only 5 minutes' walk from Jiminy Peak Mountain Resort, is proud to feature 2 outdoor tennis courts. Guests can spend their days relaxing by a heated pool or enjoying snow skiing, hiking, and lawn tennis arranged at this 3-star hotel.

A picnic area and a golf course are featured at the Jiminy Peak. A fitness centre at the hotel provides opportunities for guests to attend fitness classes.

8.5
112 reviews
~ US$179 / night

Jiminy Peak Mountain Resort

74.5 km (46.3 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Heated swimming pool

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort Hancock, located only 5 minutes' walk from Jiminy Peak Mountain Resort, is proud to feature 2 outdoor tennis courts. Guests can spend their days relaxing by a heated pool or enjoying snow skiing, hiking, and lawn tennis arranged at this 3-star hotel.

A picnic area and a golf course are featured at the Jiminy Peak. A fitness centre at the hotel provides opportunities for guests to attend fitness classes.

8.5
112 reviews
From US$ 179 / night
Holiday Inn & Suites Pittsfield-Berkshires By Ihg Holiday Inn & Suites Pittsfield-Berkshires By Ihg

Holiday Inn & Suites Pittsfield-Berkshires By Ihg

One West Street
78.9 km (49.0 mi) from Chesterfield
  • Restaurant
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Live entertainment
  • Heated swimming pool

Holiday Inn & Suites Pittsfield-Berkshires By Ihg features spacious rooms 13 minutes' walk from Samuel Harrison House. Guests can enjoy an American restaurant and a sunbathing terrace, spa therapy, and a golf course at the hotel, located near a train station.

A heated indoor pool is featured onsite.

7.2
232 reviews
~ US$99 / night

Holiday Inn & Suites Pittsfield-Berkshires By Ihg

78.9 km (49.0 mi) from Chesterfield
  • Restaurant
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Live entertainment
  • Heated swimming pool

Holiday Inn & Suites Pittsfield-Berkshires By Ihg

Holiday Inn & Suites Pittsfield-Berkshires By Ihg features spacious rooms 13 minutes' walk from Samuel Harrison House. Guests can enjoy an American restaurant and a sunbathing terrace, spa therapy, and a golf course at the hotel, located near a train station.

A heated indoor pool is featured onsite.

7.2
232 reviews
From US$ 99 / night

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

(1003 Reviews)

From 122$
Vacation Village In The Berkshires

8.6 / 10

(1287 Reviews)

From 135$
Vikings Villages Resort

9.8 / 10

(447 Reviews)

From 287$
Holiday Inn Express Hotel & Suites Brattleboro By Ihg

8.7 / 10

(161 Reviews)

From 100$

Location