Chesterfield Holidays

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Top Flight + Hotel Deals in Chesterfield

Price found within the past 48 hours. Click for updated prices.
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
Seaport District
per person
18 Sept - 22 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (3,781 reviews)
Pool was great. Close to seaport.

Reviewed on 7 Aug 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
19 Sept - 22 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on 3 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
19 Sept - 22 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on 5 Aug 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
19 Sept - 22 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Very convenient boutique hotel

Reviewed on 5 Aug 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
per person
19 Sept - 22 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (428 reviews)
Had an amazing time at the Whitney. Front desk service was impeccable, friendly and was ‘just’ the added touch I would expect of a property of this caliber. I really do look forward to my next time in Boston and hope to stay at the Whitney.

Reviewed on 25 Jul 2025

Top hotels in Chesterfield

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 €91 per night from 24 Aug to 25 Aug
€91
24 Aug - 25 Aug
includes taxes & fees
7/10 Good! (1,002 reviews)
"My daughter and the kids said it was perfect for their overnight stay after visiting Six Flags."

Reviewed on 7 Aug 2025

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
8.8/10 Excellent! (543 reviews)
"Very spacious room with full kitchen. Definitely worth the price. Would use again"

Reviewed on 5 Aug 2025

Get rates
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 €129 per night from 11 Aug to 12 Aug
€129
11 Aug - 12 Aug
includes taxes & fees
9.2/10 Wonderful! (2,239 reviews)
"Nice hotel with mediocre breakfast"

Reviewed on 1 Aug 2025

D. Hotel Suites & Spa
See all 465 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 €819 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.