Chesterfield Vacation Packages 2026 from $354

Chesterfield flight + hotel vacation packages

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

The Centennial

Save 100% on your flight

$354

per person

Sep 12 - Sep 14

found 24 hours ago

Roundtrip flight included

Baltimore (BWI) 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.

The Village of Loon Mountain Fixed Rooms

$393

per person

Sep 11 - Sep 13

found 1 day ago

Roundtrip flight included

Baltimore (BWI) 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.

Mountain View Grand Resort & Spa

$467

per person

Sep 11 - Sep 13

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Manchester (MHT)

This smoke-free hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 4 outdoor tennis courts and perks like free WiFi. Enjoy the indoor pool and unwind at the bar/lounge and poolside bar.

The Village of Loon Mountain

$408

per person

Sep 11 - Sep 13

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Manchester (MHT)

2 indoor pools, 12 outdoor tennis courts, and a hot tub are all featured at this smoke-free aparthotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the seasonal outdoor pool and conveniences like a fireplace in the lobby and laundry facilities.

Cold Spring Plymouth Resort

$408

per person

Sep 11 - Sep 13

found 1 day ago

Roundtrip flight included

Baltimore (BWI) 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.

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

$119 nightly

$129 total

Jul 12 - Jul 13

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.

Pool

Breakfast included

Best Western Plus Keene Hotel

401 Winchester St Keene NH

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$138 total

Jul 12 - Jul 13

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.

Pool

Breakfast included

Latchis Hotel

50 Main Street Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$133 total

Jul 12 - Jul 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.

Pet friendly

Parking included

Colonial Motel

889 Putney Rd Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$84 total

Aug 2 - Aug 3

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 buffet breakfast and WiFi in public areas. A garden, a grocery/convenience store, and a lobby fireplace are also on offer.

Breakfast included

Pet friendly

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$134 total

Jul 15 - Jul 16

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.

The Putney Inn

57 Putney Landing Rd Putney VT

Free Cancellation

Reserve now, pay when you stay

$138 nightly

$151 total

Jul 12 - Jul 13

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.

Don't see what you're looking for?

See all available properties in Chesterfield

View all properties

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.

See properties

Frequently asked questions

How much are vacation packages to Chesterfield?

You can pick up an excellent hotel + flight bundle for a mere $354. 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.