Chesterfield Vacation Packages

On the lookout for unbeatable Chesterfield tickets? Save time and cash by letting the dedicated staff at Orbitz package up your flights and hotels. Bundling your bookings is a perfect way to save cash. Pick out your preferred hotels, airfares, rental cars and experiences for savings of around $374! With 500 airlines to select from, you'll be up and away in no time! Also, if you're unsure where you'll stay, we've got an impressive database of more than 500,000 accommodations worldwide. When it comes to putting together the escape you've been dreaming about, you have infinite options with Orbitz.

Where is Chesterfield?

Losing your way in a foreign place always sounds romantic. But if you'd prefer to get to Chesterfield on the first try, listen up. It's a neighborhood of Keene. You'll discover it 10 miles west of the downtown area. There are around 23,000 people that call Keene home.

Places to Visit in Chesterfield

There's nothing like being in nature, and the wider region offers some sensational outdoor adventures to try. How about some snowboarding? After you've checked that off your itinerary, create more special memories by taking yourself skiing.

Car Rentals in Chesterfield

Incredible adventures are just around the corner with car rentals in Chesterfield. Ready to discover the region from the convenience and comfort of your own ride? Worrying about the cost of a cab? Pick up a vehicle right from the Dillant-Hopkins Airport area. Check out Enterprise, one of the most reliable outlets around.

Places to Visit in Chesterfield

There's nothing like being in nature, and the wider region offers some sensational outdoor adventures to try. How about some snowboarding? After you've checked that off your itinerary, create more special memories by taking yourself skiing.

Nearest Airports to Chesterfield

Manchester-Boston Regional Airport (MHT) is the nearest terminal. After you've passed through security, you'll be 50 miles from the heart of Chesterfield.

Popular Places to Visit Near Chesterfield

About 2 miles away from Chesterfield is West Chesterfield. This is a good place to visit while you are nearby, so why not make the trip and see what's on offer.

No Cancellation Fees

No matter if you've had a change of heart or your plans have gone astray for another reason, we won't request a fee if you need to cancel your booking.^ As we can't say the same for your hotel or airline, it might pay to check with them as soon as possible.

Top Chesterfield vacation package deals

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

3.5-star property

Cold Spring Plymouth Resort

9.2/10 Wonderful! (141 reviews)

Oct 24 - Oct 27

3 night stay

New Orleans (MSY) to Manchester (MHT)

American Airlines • Non-stop roundtrip • Coach

$633

per person

found 9 hours ago

My family and I have been traveling to the Lakes Region for 30+ years and have somehow never stumbled across Cold Spring Resort. I am so glad that we discovered it, as we enjoyed every bit of it. The unit that we stayed in was perfect for our family of five (two adults and three small children). The staff was extremely friendly and accommodated all of our needs. Our kids loved that there is an indoor and outdoor pool. Additionally, I loved being right on the golf course. Even though I did not get a chance to play a round, I plan to do so in the future. We will be looking into renting again next year for our annual vacation to the area.

Reviewed on Aug 9, 2025

4.0-star property

The Centennial

8.8/10 Excellent! (1,001 reviews)

Oct 11 - Oct 18

7 night stay

Columbus (CMH) to Manchester (MHT)

Southwest Airlines • Non-stop • Coach

Manchester (MHT) to Columbus (CMH)

American Airlines • Non-stop • Coach

Save 100% on your flight

$1,120

per person

found 17 hours ago

We had great stay. Spacious rooms and bathroom. Delicious restaurant. Clean. Very friendly and helpful staff.

Reviewed on Aug 11, 2025

2.5-star property

Perry's Motel and Cottages

8.4/10 Very Good! (351 reviews)

Oct 10 - Oct 17

7 night stay

New Orleans (MSY) to Manchester (MHT)

American Airlines • Non-stop roundtrip • Coach

$1,264

per person

found 8 hours ago

Great little vintage cottage in the heart of the White Mountains. The cottage was small and pretty old but the beds were comfy. My grandkids really enjoyed the pool and playing with the owners’ children. In fact, the kids kept saying they wished they lived there!

Reviewed on Jul 22, 2025