Chesterfield Vacation Packages 2025/2026 from $332

Chesterfield flight + hotel vacation packages

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

Winnisquam Lake Inn

$332

per person

Dec 27 - Jan 2

found 21 hours ago

Roundtrip flight included

Orlando (MCO) to Manchester (MHT)

This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A terrace, a library, and a picnic area are also on offer.

Cold Spring Plymouth Resort

Save 100% on your flight

$507

per person

Dec 27 - Jan 2

found 21 hours ago

Roundtrip flight included

Orlando (MCO) 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.

Hideaway Inn Mt.Sunapee

Save 100% on your flight

$679

per person

Dec 27 - Jan 2

found 21 hours ago

Roundtrip flight included

Orlando (MCO) to Manchester (MHT)

An indoor pool, free self parking, and a virtual front desk are featured at this hotel. WiFi in public areas is free. A lobby fireplace, a communal living room, and express check-out are also on offer.

Moultonborough Inn

Save 100% on your flight

$459

per person

Dec 27 - Jan 2

found 21 hours ago

Roundtrip flight included

Orlando (MCO) to Manchester (MHT)

Free WiFi in public areas is available at this lodge. Take advantage of the free self parking.

Hampton Inn & Suites Tilton

$527

per person

Dec 27 - Jan 2

found 21 hours ago

Roundtrip 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 and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Top Chesterfield hotels deals

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$91 nightly

$100 total

Dec 7 - Dec 8

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

The White House Inn

178 Route 9 East Wilmington VT

$189 nightly

$208 total

Nov 17 - Nov 18

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. A terrace and a garden are also provided.

Parking included

Free WiFi

Days Inn by Wyndham Keene NH

3 Ash Brook Road, Keene, NH

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$119 total

Nov 23 - Nov 24

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

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$104 nightly

$115 total

Nov 18 - Nov 19

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

Latchis Hotel

50 Main Street Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$139 total

Nov 17 - Nov 18

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

The Covered Bridge Inn

1043 Putney Road Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$85 total

Nov 20 - Nov 21

Total with taxes and fees

This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.

Breakfast included

Parking 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.

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 $332. 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.