Chesterfield Holidays from AU$1,071
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Your Chesterfield Holiday
Our Chesterfield holiday packages offer endless opportunities to delve into new sights, sounds and experiences. And with all your travel plans taken care of, you can kick back and enjoy your city getaway to the fullest. If your trip to Chesterfield includes some sightseeing, take in famous attractions like Chesterfield Gorge, Swift River and Petticoat Hill. Browse Expedia's extensive range of travel options and start organising your dream holiday to Chesterfield today.
The Latest Chesterfield Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront
North End
Price was AU$1,452, price is now AU$1,071 per person
AU$1,071
per person
29 Dec - 1 Jan
found 1 day ago
Return direct flight included
Memphis (MEM) to Boston (BOS)
8.6/10 Excellent! (1,687 reviews)
Perfect location, modern and nice surroundings.
Reviewed on 17 Oct 2025
The Whitney Hotel
Beacon Hill
Price was AU$1,829, price is now AU$1,226 per person
AU$1,226
per person
29 Dec - 1 Jan
found 1 day ago
Return direct flight included
Memphis (MEM) to Boston (BOS)
9.6/10 Exceptional! (475 reviews)
Love to the room, it was perfect for what we needed. Excellent service and excellent location. We will definitely stay here again.
Reviewed on 13 Oct 2025
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was AU$1,997, price is now AU$1,346 per person
AU$1,346
per person
29 Dec - 1 Jan
found 1 day ago
Return direct flight included
Memphis (MEM) to Boston (BOS)
9.6/10 Exceptional! (1,008 reviews)
A beautiful and pristine hotel. All staff were professional, welcoming, and organised. The hotel is really well located. The house toiletries are gorgeous and high quality. The breakfast was delish. Thank you for having us.
Reviewed on 18 Oct 2025
The Newbury Boston
Back Bay
Price was AU$1,868, price is now AU$1,275 per person
AU$1,275
per person
29 Dec - 1 Jan
found 1 day ago
Return direct flight included
Memphis (MEM) to Boston (BOS)
9.4/10 Exceptional! (522 reviews)
Great location but they have no concierge , and for the price you will think they would. Rooms are small
Reviewed on 8 Oct 2025
XV Beacon
Beacon Hill
Price was AU$2,212, price is now AU$1,618 per person
AU$1,618
per person
29 Dec - 1 Jan
found 1 day ago
Return direct flight included
Memphis (MEM) to Boston (BOS)
9.4/10 Exceptional! (381 reviews)
This is a classy boutique hotel, friendly staff who go the extra mile and keep the property looking sharp. The Moo restaurant is a real hotspot in the area, great food. The location is just where you wanna be in Boston.
Reviewed on 3 Oct 2025
Chesterfield Holiday
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, Calvin Theatre and Historic Northampton |
Our pick of the best Chesterfield Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$195 per night from 2 Nov to 3 Nov
AU$195
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (716 reviews)
"Yes, everything was very well set up. Thanks."
Reviewed on 19 Oct 2025
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$159 per night from 16 Nov to 17 Nov
AU$159
16 Nov - 17 Nov
includes taxes & fees
7/10 Good! (1,019 reviews)
Great hotel for a cheap night passing through town
"Over all great stay. Looking for a decent place to overnight traveling back home from a vacation. Check in process was easy and greeting immediately with a friendly staff member who appeared to be training but still very efficient at their job. We were giving directions to the elevators and went ..."
Reviewed on 13 Oct 2025
D. Hotel Suites & Spa
1 Country Club Rd, Holyoke, MA
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 22 Oct to 23 Oct
AU$196
22 Oct - 23 Oct
includes taxes & fees
9.2/10 Wonderful! (2,252 reviews)
"We’ve stayed here every fall for the past 3 years, and will continue doing so. Suite is spacious, breakfast is good, employees are kind and respectful."
Reviewed on 17 Oct 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
