Chesterfield Vacation Packages 2026 from $802

Chesterfield flight + hotel vacation packages

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

RiverWalk Resort at Loon Mountain

$802

per person

Oct 23 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Manchester (MHT)

This smoke-free hotel features an attached winery, a full-service spa, and a restaurant. Families will appreciate the arcade/game room and barbecue grills. Enjoy the outdoor pool and perks like free self parking and free WiFi.

Tiny Home Topline

$2,633

per person

Oct 9 - Oct 11

found 17 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Manchester (MHT)

This apartment featured laundry facilities and a virtual front desk. Take advantage of the free self parking.

North Conway Grand Hotel

Settlers Green

$924

per person

Oct 14 - Oct 18

found 19 hours ago

Roundtrip flight included

Nashville (BNA) to Manchester (MHT)

This hotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

The Inn at Thorn Hill & Spa

Save 100% on your flight

$2,182

per person

Oct 14 - Oct 18

found 19 hours ago

Roundtrip flight included

Nashville (BNA) 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.

Thayers Inn

$1,215

per person

Oct 9 - Oct 11

found 17 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Manchester (MHT)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A terrace, a communal living room, and a picnic area are also on offer.

Top Chesterfield hotels deals

Latchis Hotel

50 Main Street Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$127 total

Sep 10 - Sep 11

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

$84 nightly

$93 total

Sep 9 - Sep 10

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

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

$149 nightly

$162 total

Sep 22 - Sep 23

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

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$134 total

Sep 20 - Sep 21

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

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

Free Cancellation

$118 nightly

$130 total

Sep 20 - Sep 21

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

Vikings Villages Resort

360 Viking Village Drive Guilford VT

$182 nightly

$199 total

Oct 5 - Oct 6

Total with taxes and fees

A rooftop terrace is featured at this hotel, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a picnic area are also on offer.

Parking included

Free WiFi

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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.

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Frequently asked questions

How much are vacation packages to Chesterfield?

You can pick up an excellent hotel + flight bundle for a mere $802. 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.