Chesterfield Vacation Packages 2025 from $602

Chesterfield flight + hotel vacation packages

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

The Centennial

per person

Jul 24 - Jul 27

found 1 day ago

Roundtrip non-stop flight included

Las Vegas (LAS) 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.

Cold Spring Plymouth Resort

Save 100% on your flight

per person

Jul 27 - Aug 2

found 20 hours ago

Roundtrip non-stop flight included

Las Vegas (LAS) to Manchester (MHT)

A golf course and an outdoor pool are featured at this vacation home. Enjoy the indoor pool and perks like free WiFi. There's a gym on site, and laundry facilities and barbecue grills are also offered.

Moultonborough Inn

per person

Jul 27 - Aug 2

found 20 hours ago

Roundtrip non-stop flight included

Las Vegas (LAS) to Manchester (MHT)

Free WiFi in public areas is available at this lodge. Take advantage of the free self parking.

Winnisquam Lake Inn

per person

Jul 27 - Aug 2

found 20 hours ago

Roundtrip non-stop flight included

Las Vegas (LAS) to Manchester (MHT)

This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A terrace, a library, and a picnic area are also on offer.

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Save 100% on your flight

per person

Aug 23 - Aug 29

found 1 day ago

Roundtrip flight included

Fort Myers (RSW) to Manchester (MHT)

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-in. A garden, a picnic area, and express check-out are also on offer.

Top Chesterfield hotels deals

Colonial Motel And Spa

889 Putney Rd, Brattleboro, VT

Free Cancellation

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This smoke-free motel features a full-service spa, 2 indoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Hot Tub

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road, Brattleboro, VT

Free Cancellation

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This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Hampton Inn Brattleboro

1378 Putney Road, Brattleboro, VT

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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

Best Western Plus Keene Hotel

401 Winchester St, Keene, NH

Free Cancellation

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Latchis Hotel

50 Main Street, Brattleboro, VT

Free Cancellation

Reserve now, pay when you stay

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A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking and luggage storage are also offered on site.

Pet friendly

Parking included

Courtyard by Marriott Keene Downtown

75 Railroad St, Keene, NH

Free Cancellation

Reserve now, pay when you stay

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

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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 $602. 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.