Chesterfield Holidays from £953

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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.

The Latest Chesterfield Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
7 Aug - 14 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on 6 Jun 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
30 Aug - 3 Sept
found 16 hours ago
Return direct flight included
London (LON) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Location for first time Boston visitors was really good as a lot area to explore by foot then you could Uber the rest. The staff and in-room dining was outstanding

Reviewed on 16 Jun 2025

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Save 100% on your flight
per person
4 Sept - 9 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8.6/10 Excellent! (1,595 reviews)
Beautiful view. Good location

Reviewed on 16 Jun 2025

Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
Save 100% on your flight
per person
4 Sept - 9 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8.6/10 Excellent! (1,025 reviews)
Studio Alliston is a tired hotel. The staff are a mixed bag and slow. The room was dingey and smelled funny. Id stay elsewhere next time.

Reviewed on 15 Jun 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Save 100% on your flight
per person
4 Sept - 9 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8/10 Very Good! (562 reviews)
Very clean and nice! I love that Boston is rennovating building space for airport use - very needed.

Reviewed on 10 Jun 2025

Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
Save 100% on your flight
per person
4 Sept - 9 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8.8/10 Excellent! (1,865 reviews)
Nice property. Great location. Nice roof top bar and nice restaurant.

Reviewed on 21 Jun 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

Our pick of the best Chesterfield Hotel Deals

Red Roof Inn PLUS+ West Springfield
Red Roof Inn PLUS+ West Springfield
2.5 out of 5
1254 Riverdale Street, West Springfield, MA
Stay at this hotel in West Springfield. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their ...
6.8/10 (1,000 reviews)
"Amazing space clean and well maintained"

Reviewed on 10 Jun 2025

Red Roof Inn PLUS+ West Springfield
D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
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 their reviews. ...
9.2/10 Wonderful! (2,268 reviews)
"It was the perfect stay for our family for a night! It was so clean, everyone was kind, the breakfast was AMAZING & so was the indoor pool! Highly recommend!"

Reviewed on 15 Jun 2025

D. Hotel Suites & Spa
Quality Inn West Springfield
Quality Inn West Springfield
2.5 out of 5
1150 Riverdale St, West Springfield, MA
Stay at this golf hotel in West Springfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
7/10 Good! (1,001 reviews)
"I like everything cleanness, pool,staff especially very professional, cleanness of room,plus quiet ,ac runs great"

Reviewed on 16 Jun 2025

Quality Inn West Springfield
See all 467 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

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

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 £953. 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.

Discover the most popular places to visit in Chesterfield

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

* 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.