Chesterfield Vacation Packages 2026 from $479

Chesterfield flight + hotel vacation packages

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

Cranmore Mountain Lodge Bed & Breakfast

Kearsarge

$479

per person

Feb 27 - Mar 1

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Manchester (MHT)

A restaurant and a seasonal outdoor pool are featured at this bed & breakfast. Enjoy the hot tub and free perks like continental breakfast and free self parking. Free WiFi in public areas, a terrace, and a garden are also on offer.

The Centennial

$540

per person

Mar 16 - Mar 20

found 11 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Manchester (MHT)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 4 conference rooms, free WiFi in public areas, and express check-out. Guests will appreciate freebies like continental breakfast and free self parking.

Eagle Mountain House & Golf Club

$532

per person

Feb 27 - Mar 1

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Manchester (MHT)

A golf course, a 24-hour gym, and a restaurant are all featured at this historic hotel. Take advantage of ski passes on site, and enjoy cross-country skiing and snowshoeing. Enjoy the seasonal outdoor pool and unwind at the bar/lounge and poolside bar.

Quality Inn Merrimack - Nashua

$509

per person

Mar 16 - Mar 20

found 11 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Manchester (MHT)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Attitash Mountain Village

$542

per person

Feb 27 - Mar 1

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Manchester (MHT)

2 outdoor pools, 4 outdoor tennis courts, and an indoor pool are all featured at this smoke-free aparthotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Enjoy the sauna and perks like free self parking and free WiFi.

Top Chesterfield hotels deals

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$161 total

Jan 26 - Jan 27

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Pool

Hot Tub

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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

Asbury United Methodist Church

You can learn about the history of Chesterfield with a trip to Asbury United Methodist Church. Amble around the area's riverfront, or seek out its ski slopes.

Chesterfield Town Hall

After visiting Chesterfield Town Hall, make a plan to see the other sights and activities in Chesterfield. Make some time to visit the shops while you're in the area.

Frequently asked questions

How much are vacation packages to Chesterfield?

You can pick up an excellent hotel + flight bundle for a mere $479. With a Travelocity vacation package, an escape to Chesterfield has never looked so enticing! Save your time and cash and then start packing those bags.

Where can I get the best vacation package deals for Chesterfield?

Travelocity has countless ways to score an incredible Chesterfield package deal. Take your pick of 400 partner airlines and 1,000,000 properties all over the globe and craft a vacation package that suits your style. With so many options at hand, it's easy to organize your next great adventure.

Why should I book my Chesterfield vacation bundle with Travelocity?

We have a destination for every kind of globetrotter, exceptional service and customer support available 24/7. And to top all that off, we'll match any lower price you're able to find with our Price Match Guarantee.

Can I save on my Chesterfield car rental if I book it with my hotel or flight?

You certainly can — bundle your flight, car and hotel into a Chesterfield vacation package and you can save loads. With so much to see and do in and around Chesterfield, that rental vehicle will make exploring a breeze. Once you've slid into the driver's seat, get out on the wide open road and find your way to Fenway Park, a famous sight about 80 mi from Chesterfield.

Which airport is best for Chesterfield?

Chances are you'll be landing at Manchester-Boston Regional Airport (MHT), located 50 mi east of inner Chesterfield. Lebanon Municipal Airport (LEB) (50 mi away from central Chesterfield) and Rutland Southern Vermont Regional Airport (RUT) (50 mi away from central Chesterfield) are other choices.

What is there to do in Chesterfield?

Asbury United Methodist Church is one of the memorable sights that make Chesterfield a popular place to visit. But allow yourself enough time to discover the city's lesser-known attractions too. This is sometimes where the best vacation memories are created.