Chesterfield Holidays

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Top Flight + Hotel Deals in Chesterfield

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

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
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Reviewed on 28 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
18 Sept - 22 Sept
just found
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I would say this is one of the best hotel I've stayed in my life!! The room had an amazing harbor view and nice chair, comfortable bed and best amenities!! The stuff was super nice too. Definitely 5 stars!!!

Reviewed on 28 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
18 Sept - 22 Sept
just found
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on 14 Jul 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
9/10 Wonderful! (1,964 reviews)
Great location. Easy access to the City.

Reviewed on 29 Jul 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
per person
8 Oct - 12 Oct
found 19 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,087 reviews)
Check in was very good. Property sleek and minimalist. Very clean and well maintained. Shops, restaurants a few minutes walk away. Too bad the valet gives incorrect directions to local sites.

Reviewed on 29 Jul 2025

Top hotels in Chesterfield

Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way, Amherst, MA
Fully refundableReserve now, pay when you stay
The price is €146 per night from 31 Jul to 1 Aug
€146
31 Jul - 1 Aug
includes taxes & fees
8.6/10 Excellent! (1,015 reviews)
"Good and convenient for orientation at umass."

Reviewed on 20 Jul 2025

Hotel UMass
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 €110 per night from 3 Aug to 4 Aug
€110
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (2,257 reviews)
Wonderful Stay!
"My husband and I celebrated our 15 year anniversary at the D Hotel and Spa. The staff went above and beyond decorating our room making it incredibly special for us. We stayed in the one bedroom double queen suite with our two kids. The staff also included treats for our kids. This stay is something ..."

Reviewed on 26 Jul 2025

D. Hotel Suites & Spa
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is €88 per night from 10 Aug to 11 Aug
€88
10 Aug - 11 Aug
includes taxes & fees
7/10 Good! (1,012 reviews)
"Like it"

Reviewed on 28 Jul 2025

Quality Inn West Springfield
See all 466 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.

Popular places to visit

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

Frequently asked questions

How much does a Chesterfield holiday package cost?
You'll find cheap prices from €630 on Expedia for your Chesterfield getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your holiday to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
You can usually find reduced prices and greater availability in January, February and November. Browse our cheap Chesterfield holiday packages and you could get some excellent off-season deals.
How many days is enough for Chesterfield?
With a well-organised travel plan, you can easily visit the top Chesterfield sights in a handful of days. But if you'd like to venture off the beaten track or take day trips, think about booking your Chesterfield holiday for longer.
How to find the best Chesterfield package deals?
Landing a cheap Chesterfield package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Chesterfield package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chesterfield holiday as a package?
You can enjoy significant savings on your next Chesterfield retreat by booking a personalised holiday package. Click on the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Chesterfield?
If you have your Chesterfield holiday dates finalized, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Chesterfield?

  1. Pick your dates: The things you'd like to do in Chesterfield and your preferred season will help you decide when to get away.
  2. Budget wisely: Besides the cost of your stay, you'll need to factor in other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Chesterfield.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to experience in Chesterfield. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your accommodation and airfare: After you've settled on your travel dates and duration, book the right Chesterfield holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.