Chesterfield Vacation Packages 2026 from $427

Chesterfield flight + hotel vacation packages

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

The Centennial

$427

per person

Mar 26 - Mar 29

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Cranmore Mountain Lodge Bed & Breakfast

Kearsarge

$734

per person

Feb 14 - Feb 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Eagle Mountain House & Golf Club

$801

per person

Feb 14 - Feb 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Omni Mount Washington Resort & Spa

Save 100% on your flight

$1,726

per person

Feb 14 - Feb 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Manchester (MHT)

This smoke-free resort features a golf course, a full-service spa, and a nightclub. There's a free ski shuttle, and ski lessons, ski rentals and ski storage are available on site. Families will appreciate the arcade/game room and picnic area.

Attitash Mountain Village

$918

per person

Feb 14 - Feb 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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

The Covered Bridge Inn

1043 Putney Road Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$93 total

Jan 11 - Jan 12

Total with taxes and fees

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

Parking included

Free WiFi

The White House Inn

178 Route 9 East Wilmington VT

$184 nightly

$202 total

Jan 11 - Jan 12

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace and a garden are also provided.

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$136 total

Jan 11 - Jan 12

Total with taxes and fees

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.

Latchis Hotel

50 Main Street Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$136 total

Jan 12 - Jan 13

Total with taxes and fees

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.

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$161 total

Jan 19 - Jan 20

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

The Putney Inn

57 Putney Landing Rd Putney VT

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$103 total

Jan 26 - Jan 27

Total with taxes and fees

Free self parking is available and the motel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A picnic area is also provided.

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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 $427. 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.