Chesterfield Holidays from £951

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Your Chesterfield Holiday

With a holiday package to Chesterfield, say goodbye to travel planning and hello to trouble-free adventure. Every detail of your getaway has been taken care of before you go, so you can enjoy each moment discovering this interesting city. If sightseeing is part of the plan during your trip to Chesterfield, look around major attractions like Swift River, Chesterfield Gorge and Petticoat Hill. A few quick clicks is all it takes to create the ideal Chesterfield holiday on Expedia.

The Latest Chesterfield Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
13 Jun - 16 Jun
Return direct flight included
London (LHR) to Boston (BOS)
9.2/10 Wonderful! (27 reviews)
My stay was lovely. In ordering a cheese plate to await my arrival, a friend alerted the staff that it was my birthday. When I entered my very handsome room, a gorgeous little chocolate bday cake, under domed glass, sat waiting for me. Otherwise, the staff was incredibly attentive, the speakeasy was fun for a delicious cocktail, and the overall atmosphere was one of restrained indulgence. The place doesn’t feel ostentatious. Its elegance was much more understated. I loved it

Reviewed on 28 Apr 2024

The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
per person
17 Jun - 24 Jun
Return flight included
London (LHR) to Boston (BOS)
7.4/10 Good! (137 reviews)
Perfect place for my family to stay after catching the Red Sox game. Night staff was friendly and check in was easy. A good breakfast was included.

Reviewed on 2 May 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
13 Jun - 16 Jun
Return direct flight included
London (LHR) to Boston (BOS)
9.4/10 Exceptional! (264 reviews)
Huge rooms in the middle of Back Bay. Bed was so comfortable!

Reviewed on 13 Mar 2024

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
7 Jul - 11 Jul
Return flight included
London (LHR) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Excellent location!

Reviewed on 3 May 2024

Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
per person
17 Jun - 24 Jun
Return flight included
London (LHR) to Boston (BOS)
8.4/10 Very Good! (1,001 reviews)
Had a fantastic stay, staff were super accommodating, hotel and room was very clean. Grocery and pharmacy a short walk away. 10/10 would definitely return!

Reviewed on 30 Apr 2024

Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
Newton Corner
per person
17 Jun - 24 Jun
Return flight included
London (LHR) to Boston (BOS)
8.2/10 Very Good! (1,925 reviews)
heating/cooling unit very loud. I recorded it and its loud constant

Reviewed on 2 May 2024

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

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 WiFi and free parking. Our guests praise the helpful staff and the clean rooms in their ...
7.2/10 Good! (1,001 reviews)
"The staff was great"

Reviewed on 27 Apr 2024

Quality Inn West Springfield
Howard Johnson by Wyndham Amherst Hadley
Howard Johnson by Wyndham Amherst Hadley
2 out of 5
401 Russell St, Hadley, MA
Stay at this hotel in Hadley. Enjoy free breakfast, free WiFi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. Popular ...
7.2/10 Good! (1,000 reviews)
"Convenient to get around. Nice people. Room need to be updated."

Reviewed on 28 Apr 2024

Howard Johnson by Wyndham Amherst Hadley
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 free breakfast, free parking and a full-service spa. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (2,253 reviews)
Would stay again
"Overall a very nice hotel, and flexible in letting my family use the breakfast space for a small dinner gathering one evening. Our room's layout was great for 1-2 adults plus a child. Had a small issue with the thermostat in our room, plus a hotel-info QR code posted in the room came up as ..."

Reviewed on 30 Apr 2024

D. Hotel Suites & Spa
See all 414 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 £951. 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

Image for Chesterfield Gorge

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.