Chesterfield Holidays from NZ$3,222

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The Latest Chesterfield Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
per person
29 Oct - 1 Nov
found 5 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul. 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
29 Oct - 1 Nov
found 5 hours ago
Return direct flight included
Auckland (AKL) 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
per person
29 Oct - 1 Nov
found 5 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Very convenient boutique hotel

Reviewed on 5 Aug. 2025

The Hotel Salem

The Hotel Salem

3 out of 5
per person
29 Oct - 1 Nov
found 5 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9.2/10 Wonderful! (1,013 reviews)
Check in was friendly and quick, staff.was helpful with transportation options and suggestions for activities, dining and shopping. The hotel is literally next to shopping, dining and short walking distance to popular attractions.

Reviewed on 7 Aug. 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
per person
29 Oct - 1 Nov
found 5 hours ago
Return direct flight included
Auckland (AKL) 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

Chesterfield Holiday

Our pick of the best Chesterfield Hotel Deals

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! (547 reviews)
"Amazing place to stay. Can’t wait to go again."

Reviewed on 8 Aug. 2025

Get rates
Berkshire Mountain Lodge
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 NZ$178 per night from 24 Aug to 25 Aug
NZ$178
24 Aug - 25 Aug
includes taxes & fees
7/10 Good! (1,008 reviews)
"Staff was very friendly. The price was right"

Reviewed on 4 Aug. 2025

Quality Inn West Springfield
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 NZ$252 per night from 18 Aug to 19 Aug
NZ$252
18 Aug - 19 Aug
includes taxes & fees
9.2/10 Wonderful! (2,243 reviews)
"Liked it so much, that I booked another stay"

Reviewed on 6 Aug. 2025

D. Hotel Suites & Spa
See all 461 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.

Frequently asked questions

How much does a Chesterfield holiday package cost?
You'll find cheap prices from NZ$3,222 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.