Chesterfield Vacation Packages 2025/2026 from $457

Chesterfield flight + hotel vacation packages

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

Winnisquam Lake Inn

$457

per person

Nov 19 - Nov 24

found 1 day ago

Roundtrip flight included

Indianapolis (IND) 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.

The Centennial

$589

per person

Nov 19 - Nov 24

found 1 day ago

Roundtrip flight included

Indianapolis (IND) 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 Grand at Bedford Village Inn

$972

per person

Nov 19 - Nov 24

found 1 day ago

Roundtrip flight included

Indianapolis (IND) to Manchester (MHT)

A full-service spa, 3 restaurants, and an outdoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free valet parking.

Holiday Inn Express Durham by IHG

$473

per person

Nov 28 - Dec 1

found 1 day ago

Roundtrip non-stop flight included

Tampa (TPA) to Manchester (MHT)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

Extended Stay America Suites - Nashua - Merrimack

$620

per person

Nov 19 - Nov 24

found 1 day ago

Roundtrip flight included

Indianapolis (IND) 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-out. Laundry facilities are provided for your convenience.

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

$101 nightly

$110 total

Nov 3 - Nov 4

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

Econo Lodge Brattleboro

515 Canal St, Brattleboro, VT

Free Cancellation

Reserve now, pay when you stay

$68 nightly

$75 total

Oct 12 - Oct 13

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this motel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A business center, a grocery/convenience store, and a picnic area are also on offer.

Pool

Breakfast included

The Covered Bridge Inn

1043 Putney Road, Brattleboro, VT

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$139 total

Oct 8 - Oct 9

Total with taxes and fees

This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.

Breakfast included

Parking included

Latchis Hotel

50 Main Street, Brattleboro, VT

$134 nightly

$148 total

Nov 2 - Nov 3

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

Best Western Plus Keene Hotel

401 Winchester St, Keene, NH

Free Cancellation

Reserve now, pay when you stay

$140 nightly

$152 total

Nov 3 - Nov 4

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

Days Inn by Wyndham Keene NH

3 Ash Brook Road, Keene, NH

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$110 total

Nov 4 - Nov 5

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.

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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 $457. 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.