Chesterfield Holidays from £859

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Your Chesterfield Holiday

Skip the stress of organising your next big adventure with a Chesterfield holiday package. Whether you're in town for its art, food, architecture or something else, this city offers countless exciting experiences to delve into. A trip to Chesterfield is an excellent opportunity to take in the sights. Check out renowned attractions like Chesterfield Gorge, Swift River and Petticoat Hill. Your perfect Chesterfield holiday is just clicks away. Explore hotels, flights and more on Expedia for a trip that's tailored to suit your style.

Top Chesterfield Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was £1,146, price is now £859 per person
£859
per person
6 Apr - 12 Apr
found 1 day ago
Return direct flight included
Manchester (MAN) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
2nd time staying, great location, nice hotel.

Reviewed on 11 Feb 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £2,746, price is now £1,635 per person
£1,635
per person
7 Apr - 12 Apr
found 1 day ago
Return direct flight included
Manchester (MAN) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on 25 Jan 2026

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
Price was £1,951, price is now £1,221 per person
£1,221
per person
4 May - 11 May
just found
Return flight included
London (LON) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave..

Reviewed on 2 Feb 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £2,510, price is now £1,752 per person
£1,752
per person
6 Apr - 12 Apr
found 1 day ago
Return direct flight included
Manchester (MAN) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Attention to guest needs.

Reviewed on 8 Feb 2026

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £4,071, price is now £2,956 per person
£2,956
per person
4 May - 11 May
just found
Return flight included
London (LHR) to Boston (BOS)
9.4/10 Exceptional! (536 reviews)
Staff was friendly and flexible ! Rooms were spacious and beautiful, the housekeeping was not as clean or organized or detailed as other places I’ve been to but still good

Reviewed on 4 Jan 2026

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Chesterfield Essential Information

Language
English
Currency
U.S dollars
Population
1,200
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Academy of Music Theatre, Historic Northampton and Calvin Theatre

Top hotels in Chesterfield

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,239 reviews)
Check-in man was superb. Good bed. Quiet room. Wish they wouldn't use strong floor cleaner in public areas, probably Fabulosa. We tried not to breath while in the elevator, especially. Many people find this cleaner noxious. Last, clean room but lack of any carpeting made it feel less than cozy.

Reviewed on 7 Feb 2026

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D. Hotel Suites & Spa
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is £110 per night from 17 Feb to 18 Feb
£110
17 Feb - 18 Feb
includes taxes & fees
9/10 Wonderful! (838 reviews)
Perfect location, big rooms, nice staff.

Reviewed on 10 Feb 2026

Berkshire Mountain Lodge
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
400 Russell St Hadley MA
Fully refundableReserve now, pay when you stay
The price is £93 per night from 8 Mar to 9 Mar
£93
8 Mar - 9 Mar
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
Very courteous staff and a nice, clean room. Great hot breakfast. Only complaint-the pool too cold! Would definitely recommend.

Reviewed on 10 Feb 2026

Comfort Inn & Suites
See all 515 properties in Chesterfield
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.
All Inclusive Holidays
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Popular places to visit

Chesterfield Gorge

Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forests while you're in the area.

Chesterfield Gorge

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.