Chesterfield Vacation Packages 2026 from $443

Chesterfield flight + hotel vacation packages

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

Christmas Farm Inn and Spa

$443

per person

Oct 22 - Oct 25

found 3 hours ago

Roundtrip flight included

San Juan (SJU) to Manchester (MHT)

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Bring the family and enjoy the children's pool, playground, and kid-friendly dining. Enjoy the gym and perks like free self parking and free WiFi.

Mountain View Grand Resort & Spa

$692

per person

Oct 22 - Oct 25

found 3 hours ago

Roundtrip flight included

San Juan (SJU) to Manchester (MHT)

This smoke-free hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 4 outdoor tennis courts and perks like free WiFi. Enjoy the indoor pool and unwind at the bar/lounge and poolside bar.

Cranmore Mountain Lodge Bed & Breakfast

Kearsarge

$1,336

per person

Oct 17 - Oct 24

found 10 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Manchester (MHT)

A restaurant and a seasonal outdoor pool are featured at this bed & breakfast. Enjoy the hot tub and free perks like full breakfast and free self parking. Free WiFi in public areas, a terrace, and a garden are also on offer.

North Conway Grand Hotel

Settlers Green

$619

per person

Oct 22 - Oct 25

found 3 hours ago

Roundtrip flight included

San Juan (SJU) 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.

Attitash Mountain Village

$586

per person

Oct 22 - Oct 25

found 3 hours ago

Roundtrip flight included

San Juan (SJU) to Manchester (MHT)

2 outdoor pools, 4 outdoor tennis courts, and an indoor pool are all featured at this smoke-free aparthotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Enjoy the sauna and perks like free self parking and free WiFi.

Top Chesterfield hotels deals

Latchis Hotel

50 Main Street Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$141 nightly

$155 total

Sep 14 - Sep 15

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 13 - Sep 14

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

Free Cancellation

Reserve now, pay when you stay

$141 nightly

$153 total

Sep 14 - Sep 15

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

$200 nightly

$219 total

Oct 6 - Oct 7

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 $443. 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.