Chesterfield Holidays from £1,073

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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.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was £1,486, price is now £1,073 per person
£1,073
per person
13 Aug - 18 Aug
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on 23 May 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £2,760, price is now £1,997 per person
£1,997
per person
20 Sept - 24 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
From the moment I checked in with Natalie, our 4 days were superb! Natalie was so friendly and explained the property and amenities (our first time there). Even though I researched the property, and am originally from close to Boston, it was the 4th of July weekend, and there was Sooo much going on. Head concierge Nathan provided lots of tips about the best places to see certain events. So helpful. Our room was beautiful and well appointed. I miss the days of the shower cap, sewing kit, slippers, robes, etc. and they provided all that. The bed was extremely comfortable and the housekeeping staff wonderful. We go to Boston a few times a year and will be looking forward to returning here. Fabulous location!

Reviewed on 8 Jul 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was £2,288, price is now £1,662 per person
£1,662
per person
11 Sept - 16 Sept
found 12 hours ago
Return direct flight included
London (LON) to Boston (BOS)
10/10 Exceptional! (9 reviews)
I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler

Reviewed on 8 Oct 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was £1,961, price is now £1,429 per person
£1,429
per person
13 Aug - 18 Aug
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
9.6/10 Exceptional! (576 reviews)
The Whitney Hotel, was excellent stay for us. The location was prime and the staff was very helpful. Specifically the waiters on the restaurant side. Thank you.

Reviewed on 8 Jul 2026

The Cape Club Resort

The Cape Club Resort

2 out of 5
Price was £1,500, price is now £1,094 per person
£1,094
per person
28 Aug - 3 Sept
found 4 hours ago
Return flight included
London (LON) to Boston (BOS)
9.4/10 Exceptional! (3 reviews)
Great place

Reviewed on 6 Jul 2026

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

Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Fully refundable
The price is £82 per night from 21 Jul to 22 Jul
£82
21 Jul - 22 Jul
includes taxes & fees
7/10 Good! (1,012 reviews)
"The front desk during the day on Monday and Tuesday during my day was horrible very rude. Definitely should not be greeting your guest at the door."

Reviewed on 8 Jul 2026

Quality Inn West Springfield
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 £128 per night from 9 Aug to 10 Aug
£128
9 Aug - 10 Aug
includes taxes & fees
9/10 Wonderful! (1,024 reviews)
"Nice property good coffee"

Reviewed on 6 Jul 2026

Berkshire Mountain Lodge
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 £106 per night from 12 Jul to 13 Jul
£106
12 Jul - 13 Jul
includes taxes & fees
9.2/10 Wonderful! (2,129 reviews)
"Excelente hotel bonito limpio el personal muy atento y agradable la habitación grande buen aire acondicionado un desayuno variado y exquisito y acabado de preparar"

Reviewed on 7 Jul 2026

D. Hotel Suites & Spa
See all 509 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

Stay near popular Chesterfield attractions

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.
See properties

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 £1,073. 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.

Explore a world of travel with Expedia

* 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.