Chesterfield Vacation Packages 2026 from $698

Chesterfield flight + hotel vacation packages

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

Hideaway Inn Mt.Sunapee

$698

per person

Sep 26 - Oct 2

found 22 hours ago

Roundtrip flight included

Pittsburgh (PIT) to Manchester (MHT)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Bring the family and enjoy the arcade/game room, along with hiking/biking trails. There's an indoor pool on site, and a fireplace in the lobby and a communal living room are also provided.

Attitash Mountain Village

Save 100% on your flight

$749

per person

Sep 26 - Oct 2

found 22 hours ago

Roundtrip flight included

Pittsburgh (PIT) 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.

The Village of Loon Mountain Fixed Rooms

Save 100% on your flight

$929

per person

Sep 26 - Oct 2

found 22 hours ago

Roundtrip flight included

Pittsburgh (PIT) to Manchester (MHT)

A seasonal outdoor pool, free self parking, and barbecue grills are featured at this aparthotel. A terrace and a picnic area are also provided.

The Village of Loon Mountain

Save 100% on your flight

$908

per person

Sep 26 - Oct 2

found 22 hours ago

Roundtrip flight included

Pittsburgh (PIT) to Manchester (MHT)

2 indoor pools, 12 outdoor tennis courts, and a hot tub are all featured at this smoke-free aparthotel. Enjoy the free ski shuttle and onsite ski storage. Enjoy the gym and perks like free self parking and free WiFi.

Eagle Mountain House & Golf Club

Save 100% on your flight

$868

per person

Sep 26 - Oct 2

found 22 hours ago

Roundtrip flight included

Pittsburgh (PIT) 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.

Top Chesterfield hotels deals

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$130 total

Sep 1 - Sep 2

Total with taxes and fees

This hotel features an indoor pool and a gym. 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.

Colonial Motel

889 Putney Rd Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$93 total

Aug 26 - Aug 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 garden, a grocery/convenience store, and a lobby fireplace are also on offer.

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$105 total

Sep 16 - Sep 17

Total with taxes and fees

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 24-hour business center. There's a gym on site, and a snack bar/deli and a picnic area are also provided.

Latchis Hotel

50 Main Street Brattleboro VT

$120 nightly

$132 total

Aug 27 - Aug 28

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

$113 nightly

$124 total

Sep 8 - Sep 9

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.

Best Western Plus Keene Hotel

401 Winchester St Keene NH

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$162 total

Aug 26 - Aug 27

Total with taxes and fees

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.

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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.

Stay near popular Chesterfield attractions

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.

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Frequently asked questions

How much are vacation packages to Chesterfield?

You can pick up an excellent hotel + flight bundle for a mere $698. 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.