Chesterfield Vacation Packages 2026 from $472

Chesterfield flight + hotel vacation packages

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

Hampton Inn & Suites Manchester-Bedford

$472

per person

Sep 30 - Oct 3

found 11 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Manchester (MHT)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like on-the-go breakfast and free self parking.

Nootka Lodge

$772

per person

Sep 30 - Oct 5

found 10 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Manchester (MHT)

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

White River Inn and Suites

$527

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Manchester (MHT)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's an indoor pool on site, and a 24-hour front desk and a terrace are also provided.

The Lake Estate on Winnisquam

$1,157

per person

Sep 30 - Oct 3

found 11 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Manchester (MHT)

This luxury hotel features a private beach, a full-service spa, and 2 restaurants. Traveling on business? Take advantage of the free WiFi in public areas and valet parking. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.

Aiken Manor B&B

$533

per person

Sep 30 - Oct 3

found 11 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Manchester (MHT)

This bed & breakfast features free WiFi in public areas, barbecue grills, and free self parking. Enjoy the free cooked-to-order breakfast each morning. A terrace, a garden, and a picnic area are also on offer.

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

$141 nightly

$153 total

Aug 30 - Aug 31

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

Colonial Motel

889 Putney Rd Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$93 total

Aug 30 - Aug 31

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.

Breakfast included

Pet friendly

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$106 total

Sep 14 - Sep 15

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.

Breakfast included

Pet friendly

Latchis Hotel

50 Main Street Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$146 nightly

$160 total

Aug 30 - Aug 31

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

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$112 nightly

$123 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.

Pool

Hot Tub

Best Western Plus Keene Hotel

401 Winchester St Keene NH

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$162 total

Aug 30 - Aug 31

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

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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.

See properties

Frequently asked questions

How much are vacation packages to Chesterfield?

You can pick up an excellent hotel + flight bundle for a mere $472. 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.