Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Save up to 17% by booking Flight + Hotel.

Search 321,000 hotels and 400 airlines worldwide.

Get the price Guarantee available for your trip.


Chester Vacation Packages

Chester is part of the city of Springfield, a major city with a population of 150,000 residents. The central business of Springfield is just 25 miles (40 kilometers) away, while Bradley International Airport can be found 30 miles (48 kilometers) to the south of Chester.

Many of Springfield’s most popular attractions are within easy reach of Chester, so it is a popular place to stay or visit on a day trip. Among the places not to miss are the marvelous Jacob's Pillow Dance and the incredible Prime Outlets Lee. Two other popular spots within a short distance of Chester are the Look Memorial Park and the Shakespeare and Company.

Those interested in exhibits and shows will find some unique cultural highlights in and around Chester. There are many excellent places visitors can pay a visit to for a couple of hours including the Norman Rockwell Museum in Stockbridge and Arrowhead Museum in Pittsfield. Experience established and up-and-coming artists live on stage at Calvin Theater in Northampton and the Academy of Music Theater.

If the weather is good head outside and make the most of the nearby parks and reserves. Nature lovers will want to check out the Smith College Botanic Garden in Northampton, where locals come to enjoy a little slice of tranquility. Head out to Mount Tom in Holyoke.

Nearby Mullins Center, Amherst is a great place to spend an afternoon enjoying college basketball, and to see local heroes, the UMass Minutemen, in all their glory. If you want to endear yourself with the locals, wear maroon and white, the colors of the UMass Minutemen.

Finding somewhere suitable to rest your head around Chester is a breeze. The Hampton Inn & Suites Berkshires Lenox, the Howard Johnson Express Inn - Lenox and the Quality Inn & Suites Northampton are just some of the best places to find a warm welcome and a good night’s rest.


Top Hotel Deals

See all 130 Hotels in Chester
£69
La Quinta Inn & Suites Springfield

La Quinta Inn & Suites Springfield

100 Congress Street, Springfield
4.0
of 5, from 385 reviews
3.0 out of 5.0

Located in the heart of Springfield, this hotel is within 1 mi (2 km) of Quadrangle and Springfield Armory. Naismith Memorial Basketball Hall of Fame is 1.4 mi (2.2 km) away.

£217
Applegate Inn

Applegate Inn

279 West Park Street, Lee
3.0 out of 5.0

Situated in Lee, this bed & breakfast is within a 15-minute walk of Greenock Country Club, Lee Library, and Animagic Museum of Animation. Lee Prime Outlets and Berkshire Theatre Festival are also within 3 mi (5 km).

£53
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

1254 Riverdale Street, West Springfield
3.7
of 5, from 185 reviews
2.5 out of 5.0

Situated near the airport, this hotel is 2.3 mi (3.8 km) from Holyoke Mall and 2.5 mi (4 km) from Josiah Day House. Springfield Armory and Naismith Memorial Basketball Hall of Fame are also within 6 mi (10 km).

Pilgrim Inn

Pilgrim Inn

165 Housatonic St, Lee
3.4
of 5, from 28 reviews
3.0 out of 5.0

Located in the heart of Lee, this hotel is within a 15-minute walk of Lee Prime Outlets, Lee Library, and Animagic Museum of Animation. Greenock Country Club is 0.8 mi (1.4 km) away.

£159
The Summer White House

The Summer White House

17 Main St, Lenox
3.0 out of 5.0

Situated in Lenox, this bed & breakfast is within a 10-minute walk of Lenox Library, Ventfort Hall Mansion and Gilded Age Museum, and Shakespeare and Company. Frelinghuysen Morris House and Studio and Tanglewood Music Center are also within 2 mi (3 km).

£55
Quality Inn & Suites Northampton-Amherst

Quality Inn & Suites Northampton-Amherst

117 Conz St, Northampton
3.5
of 5, from 110 reviews
2.5 out of 5.0

Situated in the entertainment district, this hotel is within a 15-minute walk of Calvin Theater and Academy of Music Theater. Smith College and Smith College Botanic Garden are also within 1 mi (2 km).

£115
Hotel Northampton

Hotel Northampton

36 King Street, Northampton
4.1
of 5, from 65 reviews
3.5 out of 5.0

Located in the heart of Northampton, this hotel is within a 10-minute walk of Calvin Theater, Academy of Music Theater, and Smith College. Smith College Botanic Garden and Hadley Farm Museum are also within 3 mi (5 km).

£84
D. Hotel & Suites

D. Hotel & Suites

1 Country Club Rd, Holyoke
4.5
of 5, from 329 reviews
3.0 out of 5.0

Located in the suburbs, this family-friendly hotel is 4.3 mi (7 km) from Smith College and 11.8 mi (19.1 km) from University of Massachusetts-Amherst. MassMutual Center and Naismith Memorial Basketball Hall of Fame are also within 25 mi (40 km).

Top Flight + Hotel Deals

Top Deals on Flights

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.