Chesterfield Holidays from £1,039
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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.
Sesuit Harbor House
£1,039
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
London (LHR) to Boston (BOS)
9.6/10 Exceptional! (200 reviews)
Super friendly staff right from the check in with Phil , the owner, to our last hour when I met his sweet wife while we were watching the goats eat breakfast. Room had everything we needed personalized with with a a handwritten welcome card.
Reviewed on 23 Aug 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
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
£104
30 Aug - 31 Aug
includes taxes & fees
9.2/10 Wonderful! (2,128 reviews)
"The D.Hotel was wonderful with exception of ice machine only on two floors. Took two hours to get extra pillows."
Reviewed on 23 Aug 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
£94
31 Aug - 1 Sept
includes taxes & fees
Hotel Northampton
36 King Street Northampton MA
Fully refundableReserve now, pay when you stay
£122
25 Aug - 26 Aug
includes taxes & fees
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.
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.
Chesterfield Public Library
Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops.
Chesterfield Gorge Reservation
You can take time to visit Chesterfield Gorge Reservation during your travels to Chesterfield. Amble around the area's parks or visit its shops.
Krug Sugarbush
You can take time to visit Krug Sugarbush during your travels to Chesterfield. Amble around the area's parks or visit its shops.
Chesterfield Town Hall
After visiting Chesterfield Town Hall, make a plan to see the other sights and activities in Chesterfield. Amble around the area's parks or visit its shops.
Oak Hill
Commune with nature and explore the great outdoors at Oak Hill during your travels in Chesterfield. Amble around the area's parks or visit its shops.
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 £1,039. 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.
