Chesterfield Holidays from £990

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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.
The Beverly

The Beverly

3 out of 5
per person
17 Oct - 21 Oct
found 1 day ago
Return direct flight included
London (LON) to Boston (BOS)
8.4/10 Very Good! (323 reviews)
Stopped in for overnight stay. Awkward check in as no emailed code (no desk staff on premises), got that worked out. Rooms are comfortable and appeared clean. Couple of places across street to eat and little shopping center, so nice options for quick stay.

Reviewed on 31 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
5 Sept - 8 Sept
found 16 hours ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Favorite hotel in Boston amazing pool and gym

Reviewed on 2 Aug 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
18 Oct - 25 Oct
found 17 hours ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8.8/10 Excellent! (234 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul 2025

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

2 out of 5
South End
per person
18 Oct - 25 Oct
found 17 hours ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
7.4/10 Good! (114 reviews)
Property is located in a very nice area. No frill, what they advertise, you get.

Reviewed on 23 May 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
5 Sept - 8 Sept
found 16 hours ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (1,016 reviews)
Best place to stay in boston

Reviewed on 2 Aug 2025

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
The price is £96 per night from 17 Aug to 18 Aug
£96
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (2,237 reviews)
"Nice hotel with mediocre breakfast"

Reviewed on 1 Aug 2025

D. Hotel Suites & Spa
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way, Amherst, MA
The price is £134 per night from 2 Sept to 3 Sept
£134
2 Sept - 3 Sept
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Good and convenient for orientation at umass."

Reviewed on 20 Jul 2025

Hotel UMass
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is £60 per night from 17 Aug to 18 Aug
£60
17 Aug - 18 Aug
includes taxes & fees
5.2/10 (759 reviews)
Good enough
"Comfortable for (Dad and Son) a two night trip."

Reviewed on 2 Aug 2025

FairBridge Inn Express
See all 463 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
All Inclusive Holidays
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Beach Holidays
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Family Friendly Holidays

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

Frequently asked questions

How much does a Chesterfield travel package cost?
We make it easy to see the world, with Chesterfield travel packages starting from just £990. You'll have the flexibility to bundle your preferred airlines, hotels and car rental. For the ultimate getaway, why not add a few tours and activities to your travel itinerary?
If I'm not able to travel, can I cancel my Chesterfield travel package?
Whether it's your flight or hotel, yes, you can amend or cancel it. Locked in your Chesterfield travel package in the last 24 hours? You may be able to make changes at no cost. If it's been longer than that, you may incur a charge from your hotel, airline or car rental company. For more details, look up our Customer Service Portal. We'll help you every step of the way.
How do I get a cheap travel package to Chesterfield?
It's easy. Just bundle. Flights, rental cars and hotels — combine whatever you need into a Chesterfield travel package to save loads of cash. Score even more bargains when you include extras such as activities or tours to your booking. But that's not the only good part. You have the flexibility to put together your trip your way. We offer over 550 partner airlines and 1,000,000 properties across the globe, so that everyone has an opportunity to travel and fulfil those holiday dreams.
Does Expedia offer Book Now, Pay Later Chesterfield holidays?
Yes. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply select the payment plan that suits best during checkout and take the stress out of budgeting for your next trip. Remember to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your travel buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's convenient monthly instalment plans. If paying small amounts each month sounds right for you, pick this option at checkout.
  • Pay in instalments holidays: If you'd prefer to pay for your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Clicking on the "book now" button is much easier with this plan. Just put down a small deposit on your booking and then start packing your bags.

Where should I stay in Chesterfield?
Chesterfield has numerous fascinating places to discover, such as Chesterfield Gorge. Secure a room in a hotel close by and make sightseeing easier.
What are the top hotels in Chesterfield?
Reserve a room at Boston Park Plaza. It's one of the neighbourhood's most popular properties. Another great option in Chesterfield is Embassy Suites Boston Logan Airport.
How far in advance should I book my Chesterfield holiday?
While not all air carriers advertise tickets early, it's usually possible to look up international airfares on Expedia up to a year in advance. This is the time you'll score some incredible deals. If you're purchasing tickets last minute, there's a chance you could get lucky. Low prices sometimes emerge only weeks before departure.
What does an Expedia Chesterfield travel package include?
Hotels, flights and rental cars, or any combination of the three — the choice is yours. Whether you're headed to Chesterfield with the entire family or travelling solo, there's a bundle to suit your style and budget. Once you've made your booking, why not add on one or two tours and experiences?
What should I know before booking a Chesterfield travel package?
A travel package can be tailored to your budget and is a terrific way to make your money go further. How much you include is completely up to you. Hotels, rental cars and flights — come up with a combination that suits your style.
Can I choose my airline with a Chesterfield Expedia travel package?
Yes — that's one of the best things about an Expedia travel package. You're in control. We have more than 550 partner airlines across the globe, so you have loads of choice when arranging your Chesterfield getaway.

* 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.