Chesterfield Vacations

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Top Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
34.87 km from city center
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St, West Springfield, MA
33.46 km from city center
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
34.67 km from city center
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
23.29 km from city center
Stay at this 3-star spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 out of 5
9 Greenfield Rd, South Deerfield, MA
20.47 km from city center
Stay at this hotel in South Deerfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
The Ellery

The Ellery

3.5 out of 5
259 Elm Street, Northampton, MA
17.67 km from city center
Stay at this 3.5-star hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
400 Russell St, Hadley, MA
24.36 km from city center
Book a stay at this business-friendly hotel in Hadley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street, West Springfield, MA
33.2 km from city center
Stay at this hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3 out of 5
885 Riverdale Street, West Springfield, MA
34.25 km from city center
Stay at this 3-star business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way, Amherst, MA
25.48 km from city center
Stay at this hotel in Amherst. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Mullins ...
Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

2.5 out of 5
2 Southampton Rd, Westfield, MA
29.18 km from city center
Book a stay at this business-friendly hotel in Westfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr, Chicopee, MA
32.74 km from city center
Stay at this hotel in Chicopee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Motel 6 Chicopee, MA - Springfield

Motel 6 Chicopee, MA - Springfield

2 out of 5
36 Burnett Rd, Chicopee, MA
34.77 km from city center
Stay at this motel in Chicopee. Enjoy free WiFi, a 24-hour front desk, and laundry facilities. Our guests praise the helpful staff and the clean rooms in our ...
Quality Inn Chicopee - Springfield

Quality Inn Chicopee - Springfield

2.5 out of 5
463 Memorial Dr, Chicopee, MA
32.87 km from city center
Book a stay at this business-friendly hotel in Chicopee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Big E and MGM Springfield are ...
Riverdale Inn

Riverdale Inn

2 out of 5
1500 Riverdale Street, On Route 5, West Springfield, MA
32.52 km from city center
Stay at this motel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Big E and Eastern States Exposition are ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

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

JetBlue Airways
Wed, Dec 3 - Fri, Dec 5
LAX
Los Angeles Intl.
BOS
Logan Intl.
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Dec 3 from Los Angeles Intl. to Logan Intl., returning Fri, Dec 5, priced at $217 found 2 days ago
Delta
Wed, Dec 3 - Wed, Dec 10
LAX
Los Angeles Intl.
BOS
Logan Intl.
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Dec 3 from Los Angeles Intl. to Logan Intl., returning Wed, Dec 10, priced at $217 found 2 days ago
Spirit Airlines
Tue, Dec 2 - Wed, Dec 3
LAX
Los Angeles Intl.
BOS
Logan Intl.
$229 Roundtrip, found 2 days ago
$229
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Dec 2 from Los Angeles Intl. to Logan Intl., returning Wed, Dec 3, priced at $229 found 2 days ago
American Airlines
Sat, Jan 17 - Thu, Jan 29
PDX
Portland Intl.
BOS
Logan Intl.
$279 Roundtrip, found 1 day ago
$279
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jan 17 from Portland Intl. to Logan Intl., returning Thu, Jan 29, priced at $279 found 1 day ago
Hawaiian Airlines
Wed, Dec 31 - Tue, Jan 13
PDX
Portland Intl.
BOS
Logan Intl.
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Wed, Dec 31 from Portland Intl. to Logan Intl., returning Tue, Jan 13, priced at $297 found 1 day ago