Chesterfield Vacation Packages 2025/2026 from $294

Chesterfield flight + hotel vacation packages

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

Holiday Inn Express & Suites Merrimack by IHG

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Manchester (MHT)

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Cold Spring Plymouth Resort

Save 100% on your flight

per person

Oct 17 - Oct 22

found 1 hour ago

Roundtrip flight included

Fort Myers (RSW) 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.

The Lake Estate on Winnisquam

per person

Nov 3 - Nov 6

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Manchester (MHT)

This smoke-free hotel features a private beach, a full-service spa, and 2 restaurants. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and concierge services.

Anchor at Tideline

per person

Nov 3 - Nov 6

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Manchester (MHT)

This inn features 6 restaurants and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop and a picnic area are also provided.

Inn On Golden Pond

Save 100% on your flight

per person

Oct 11 - Oct 14

found 8 hours ago

Roundtrip flight included

Atlanta (ATL) to Manchester (MHT)

This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Families will appreciate the playground, onsite laundry facilities, and free supervised childcare. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area.

Top Chesterfield hotels deals

Colonial Motel And Spa

889 Putney Rd, Brattleboro, VT

Free Cancellation

Reserve now, pay when you stay

$140 nightly

$154 total

Aug 18 - Aug 19

Total includes taxes and fees

This smoke-free motel features a full-service spa, 2 indoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Hot Tub

Keene Elm City Hotel, Ascend Hotel Collection

175 Key Rd, Keene, NH

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$136 total

Aug 24 - Aug 25

Total includes 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

Hampton Inn Brattleboro

1378 Putney Road, Brattleboro, VT

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$136 total

Sep 2 - Sep 3

Total includes 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

$138 nightly

$151 total

Aug 26 - Aug 27

Total includes 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.

Breakfast included

Pet friendly

Days Inn by Wyndham Keene NH

3 Ash Brook Road, Keene, NH

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$121 total

Aug 31 - Sep 1

Total includes 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

Best Western Plus Keene Hotel

401 Winchester St, Keene, NH

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$162 total

Aug 24 - Aug 25

Total includes 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

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.

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 $294. 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.