Chesterfield Vacation Packages 2026 from $476

Chesterfield flight + hotel vacation packages

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

Exeter Inn

$476

per person

Dec 24 - Dec 27

found 18 hours ago

Roundtrip flight included

New York (NYC) to Manchester (MHT)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free continental breakfast is served.

Hideaway Inn Mt.Sunapee

$830

per person

Nov 28 - Dec 3

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) 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.

The Inn at Thorn Hill & Spa

$823

per person

Jan 1 - Jan 3

found 18 hours ago

Roundtrip non-stop flight included

Islip (ISP) to Manchester (MHT)

This smoke-free hotel features an attached winery, a full-service spa, and 2 restaurants. Enjoy the sauna and perks like free valet parking and free WiFi. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

The Grand at Bedford Village Inn

$786

per person

Dec 24 - Dec 27

found 18 hours ago

Roundtrip flight included

New York (NYC) 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.

Temple's Sunset Harbor

Save 100% on your flight

$4,315

per person

Nov 28 - Dec 3

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Manchester (MHT)

This vacation home features barbecue grills. Take advantage of the free self parking.

Top Chesterfield hotels deals

Colonial Motel

889 Putney Rd Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$109 total

Nov 1 - Nov 2

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

Latchis Hotel

50 Main Street Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$141 nightly

$155 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

$142 nightly

$154 total

Nov 1 - Nov 2

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

The White House Inn

178 Route 9 East Wilmington VT

$184 nightly

$202 total

Nov 1 - Nov 2

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace and a garden are also provided.

Breakfast included

Parking included

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

Free Cancellation

$111 nightly

$122 total

Nov 8 - Nov 9

Total with taxes and fees

This hotel features an indoor pool, a gym, and a restaurant. 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

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$101 total

Oct 25 - Oct 26

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

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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 $476. 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.