Chesterfield Holidays

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Your Chesterfield Holiday

When a city escape is calling, answer it with a holiday package to Chesterfield. With all your travel arrangements in order before you go, all you need to do here is focus on having the time of your life. Fill your free time with tours of Spofford Lake, Asbury United Methodist Church and Madame Sherris Castle Ruins, some of the top attractions you really should see during your trip to Chesterfield. Whoever you're taking a break with and whatever the size of your budget, your ultimate Chesterfield holiday is just a few clicks away with Expedia.

Chesterfield Essential Information

Language
English
Currency
U.S dollars
Population
3,800
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Colonial Theatre, Historical Society of Cheshire County and Cheshire Childrens Museum

Top hotels in Chesterfield

Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is £114 per night from 12 Aug to 13 Aug
£114
12 Aug - 13 Aug
includes taxes & fees
6.6/10 (1,002 reviews)
"Always a pleasure to stay at the Colonial"

Reviewed on 28 Jul 2025

Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is £99 per night from 4 Sept to 5 Sept
£99
4 Sept - 5 Sept
includes taxes & fees
8/10 Very Good! (862 reviews)
"Didn’t like the fact that I was suppose to be charge when I checked in but they charged my card before I arrived."

Reviewed on 9 Aug 2025

Hampton Inn Brattleboro
Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is £101 per night from 17 Aug to 18 Aug
£101
17 Aug - 18 Aug
includes taxes & fees
8.4/10 Very Good! (875 reviews)
"Quiet stay beds are a little small"

Reviewed on 10 Aug 2025

Keene Elm City Hotel, Ascend Hotel Collection
See all 502 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?
Discover the best of Chesterfield from just . We offer a great selection of flights, rental cars and hotels to suit every budget and style. You can pick up even more discounts when you add a couple of experiences or tours to your travel package.
If I'm not able to travel, can I cancel my Chesterfield travel package?
Don't worry if you're rethinking your Chesterfield travel package — it's possible to cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We know life can sometimes throw you a curveball, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.
How do I get a cheap travel package to Chesterfield?
Browse and lock in everything in the one place with our Chesterfield travel packages. You'll find bargains on flights, hotels, tours and more that'll keep your wallet happy and your sense of adventure alive. And, with more than 550 air carriers and 1,000,000 hotel options around the world to choose from, there are endless opportunities to mix and match as you like.
Does Expedia offer Book Now, Pay Later Chesterfield holidays?
Expedia has teamed up with online lender Klarna to make your next getaway easier on your bank balance. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more cash to splash while you're away. Klarna has several payment plans to pick from, so you're sure to find one that suits your budget. Check out these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna offers just that! Paying in easy monthly instalments will make your holiday dreams possible.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in Chesterfield?
A getaway to Chesterfield wouldn't be complete without checking out Spofford Lake, Madame Sherri Forest and Asbury United Methodist Church. Spend your evenings near these tourist attractions and make sightseeing easy.
What are the top hotels in Chesterfield?
Green Granite Inn and Hampton Inn & Suites Portsmouth Downtown are among the most sought-after hotels in Chesterfield. Why not have a look at the rates and amenities at each and then make up your mind?
How far in advance should I book my Chesterfield holiday?
Reserving your tickets early with Expedia means one less thing to have to worry about. Most air carriers advertise prices up to 12 months prior to take off. Typically, this is the cheapest time to book. If circumstances have left you booking late, incredible deals to Chesterfield sometimes become available just weeks before departure.
What does an Expedia Chesterfield travel package include?
Much of that is up to you. You can select from a range of Chesterfield packages, such as a flight, rental car and hotel. You can also book a flight with a hotel, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like activities and experiences. Whatever your dream Chesterfield trip looks like, get set to save!
What should I know before booking a Chesterfield travel package?
A package can be cheaper than individually booking everything you need for your getaway. For example, combine your flights, hotels and rental cars and save a tidy sum. Whatever your holiday plans, you're sure to find a package that best suits your budget.
Can I choose my airline with a Chesterfield Expedia travel package?
You certainly can. We have more than 550 airline partners around the world, so choose the carrier that matches your travel needs.

* 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.