Chesterfield Vacation Packages

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Your Chesterfield Vacation

Skip the stress of organizing your next big adventure with a Chesterfield vacation package. Whether you're in town for its art, food, architecture or something else, this city offers countless exciting experiences to delve into. A trip to Chesterfield is an excellent opportunity to take in the sights. Check out renowned attractions like Chesterfield Gorge, Swift River and Petticoat Hill. Your perfect Chesterfield vacation is just clicks away. Explore hotels, flights and more on Expedia for a trip that's tailored to suit your style.

Top Chesterfield Vacation Deals

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
amazing staff and service, polite, friendly,

Reviewed on Apr. 16, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul. 12 - Jul. 15
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.2/10 Wonderful! (27 reviews)
Very good service. Furniture in all areas and the room is low and petite. Not comfortable. Bedding is comfortable. Food on Long Bar was well prepared. However presentation is pedestrian. Ordered Avacado Toast. Tasty, but arrived on a small plate. No garnish, no fruit etc. overall good stay.

Reviewed on Apr. 8, 2024

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
9.8/10 Exceptional! (274 reviews)
My husband and I spent one night at The Whitney and were extremely pleased with our stay. The room was lovely and the staff were very nice and helpful. We would absolutely return and recommend it without hesitation.

Reviewed on Mar. 24, 2024

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
8.6/10 Excellent! (1,448 reviews)
Beautiful lobby, great staff, big rooms, and comfy beds. Will be back!

Reviewed on Apr. 19, 2024

YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
8.2/10 Very Good! (1,617 reviews)
Great location - visited for Boston Marathon and it was perfect 👌

Reviewed on Apr. 18, 2024

Prices and availability subject to change. Additional terms may apply.

Chesterfield Hotel Deals

D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
Fully refundable
The price is CA $174 per night from Apr. 24 to Apr. 25
CA $174
CA $200 total
includes taxes & fees
Apr 24 - Apr 25
9.2/10 Wonderful! (2,233 reviews)
"Loveable staff well manmered all the time peaceful space well maintained cleaning staff well respected and lots of manners"

Reviewed on Apr. 17, 2024

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 CA $132 per night from May 20 to May 21
CA $132
CA $148 total
includes taxes & fees
May 20 - May 21
7.2/10 Good! (1,000 reviews)
Have stayed many times, good value, comfy room!
"When I visit Six Flags, I always stay here, have visited several times over the years, and this stay was about the same as before, but a few more issues. First the good, I had a 2 queen room on 4th floor, #425, and room was spacious, comfortable overall, TV worked well, as did HVAC, and beds were ..."

Reviewed on Apr. 16, 2024

Quality Inn West Springfield
Red Roof Inn PLUS+ West Springfield
Red Roof Inn PLUS+ West Springfield
2.5 out of 5
1254 Riverdale Street, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $116 per night from Apr. 21 to Apr. 22
CA $116
CA $130 total
includes taxes & fees
Apr 21 - Apr 22
7/10 Good! (1,000 reviews)
"This inn isn't fancy, but it met all my expectations for cleanliness and comfort."

Reviewed on Apr. 12, 2024

Red Roof Inn PLUS+ West Springfield
See all 411 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
Less than you might think — from a low CA $820, as a matter of fact! By combining flights, hotels and car rentals into a custom-made vacation package, your Chesterfield escape is just clicks away.
How do I get a cheap travel package to Chesterfield?
One word: bundle. Hotels, rental cars and flights — combine whatever you need into a Chesterfield vacation package to save loads of cash. Score even more deals when you add extras such as activities or tours to your booking. But that’s not the only good part. You have the flexibility to tailor your vacation your own way. We offer over 550 partner airlines and 1,000,000 properties globally, so that everyone has a chance to travel and fulfill those vacation fantasies.
Where should I stay in Chesterfield?
If you plan to visit Chesterfield Gorge, forget about commuting and lock in a hotel close by. It’s one of the most popular attractions in Chesterfield.
How far in advance should I book my Chesterfield vacation?
It all depends on the air carrier, but it’s usually possible to look up international fares on Expedia up to a year in advance. While it’s advisable to book ahead of time, lucky customers will sometimes nab a cheaper flight just weeks prior to departure dates.
What does an Expedia Chesterfield travel package include?
Rental cars, hotels and flights, or any combination of the three — the choice is all yours! Whether you’re headed to Chesterfield with the whole family or traveling with your friends, there’s a bundle to fit your style and budget. Once you’ve made your booking, why not add on some tours and experiences?
What should I know before booking a Chesterfield travel package?
You’ll save plenty with an Expedia travel package. Bundle your flights, rental cars and hotels and land great discounts. You’re not limited to hotels, however. Book with us and take your pick of beachside condos, creek-side mountain cabins and even ranches and treehouses!
Can I choose my airline with a Chesterfield Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you want to fly to Chesterfield in economy or first class, simply select from the available airline options. Expedia has access to more than 550 airline partners around the world.
If I'm not able to travel, can I cancel my Chesterfield vacation package?
Yes, you can. We understand that life happens, so we’re here to help if you have to make changes to your Chesterfield vacation package. You may be able to cancel or change your itinerary for free if you’ve booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Chesterfield

Image for Chesterfield Gorge

Chesterfield Gorge

Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forest while you're in the area.

Chesterfield Gorge

Other vacations you might like

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