Chesterfield Vacations from $553
Book a Hotel + Flight or Car together to unlock savings
Your Chesterfield Vacation
When a city escape is calling, answer it with a vacation package to Chesterfield. With all your travel arrangements in order before you go, all you need to do here is focus on having the time of your life. Fill your free time with tours of Spofford Lake, Asbury United Methodist Church and Madame Sherris Castle Ruins, some of the top attractions you really should see during your trip to Chesterfield. Whoever you're taking a break with and whatever the size of your budget, your ultimate Chesterfield vacation is just a few clicks away with Expedia.
The Latest Chesterfield Vacation Packages
- Stonybrook Motel & Lodge
Jan 15 - Jan 18Stonybrook Motel & Lodge + Flight
Franconia3 nights2.0 star property7.6/10 - Good (1,003 reviews)"No pool! And a run down property. I did not get the deluxe double room that I booked on Hotels.com (Expedia on their end). He said this is the 3rd time it has happened. I told him to call and fix it. He knows. He at first gave me a queen room when my booking was 2 beds. Then switched to a 2 bed room but so bad! The toilet overflowed from the tank and he came and did not fix it. Did again the next day. He should have given me the nice room that i n"Reviewed November 11, 2026Roundtrip • Houston (HOU) - Manchester (MHT)HOU - MHT • 1 stop MHT - HOU • 1 stop$797$553found 9 hours agoper traveler - The Village of Loon Mountain Fixed Rooms
Jan 15 - Jan 18The Village of Loon Mountain Fixed Rooms + Flight
Lincoln3 nights2.0 star property8.6/10 - Excellent (73 reviews)"Check-in process was worse . We had late check-in . No one was there at the counter. The phone which was supposed to give the code to get the key was not working. We waited there for more than 3 hours in the cold till 11:30 pm. I would not recommend this place ."Reviewed October 30, 2026Roundtrip • Houston (HOU) - Manchester (MHT)HOU - MHT • 1 stop MHT - HOU • 1 stop$1,077$793found 9 hours agoper traveler - The Village of Loon Mountain
Jan 15 - Jan 18The Village of Loon Mountain + Flight
Lincoln3 nights3.0 star property8.6/10 - Excellent (635 reviews)"very spacious and it was very clean"Reviewed November 11, 2026Roundtrip • Houston (HOU) - Manchester (MHT)HOU - MHT • 1 stop MHT - HOU • 1 stop$1,208$897found 9 hours agoper traveler - The Grand at Bedford Village Inn
Dec 26 - Jan 1The Grand at Bedford Village Inn + Flight
Bedford6 nights5.0 star property9.6/10 - Exceptional (407 reviews)Roundtrip • Tampa (TPA) - Manchester (MHT)TPA - MHT • Nonstop MHT - TPA • 1 stop$2,087$1,631found 18 hours agoper traveler - Riverhouse by Weekender (Formerly Jack Daniels Inn)
Dec 18 - Dec 21Riverhouse by Weekender (Formerly Jack Daniels Inn) + Flight
Peterborough3 nights2.5 star property9.2/10 - Wonderful (482 reviews)Roundtrip • San Juan (SJU) - Manchester (MHT)SJU - BOS • Nonstop BOS - SJU • Nonstop$793$661found 1 day agoper traveler
Where to stay near Chesterfield
Brattleboro
Discover Brattleboro, a welcoming destination perfectly suited for travelers seeking a blend of nature and adventure. With its scenic landscapes, Brattleboro offers access to skiing and outdoor activities, along with attractions like the charming Brattleboro Common, the stunning Hogback Mountain Conservation Area, and the intriguing Southern Vermont Natural History Museum. Located about 9 miles by car from Chesterfield, Brattleboro makes for a smart choice for your next getaway, providing a rich experience for families and outdoor enthusiasts alike.
Keene
Experience the charm of Keene, a vibrant hub for travelers seeking cultural and outdoor adventures. This delightful city offers attractions like the scenic Historic Main Street, the educational atmosphere of Keene State College, and the lush landscapes of Stonewall Farm, making it perfect for family outings and nature enthusiasts alike. Located about 11 miles by car from Chesterfield, Keene provides easy access to a variety of activities year-round, ensuring a smart choice for your next getaway.
West Chesterfield
If you are a nature and adventure enthusiast, look no further than West Chesterfield, a charming destination known for its outdoor experiences and family-friendly atmosphere. Visitors can enjoy the stunning landscapes of Spofford Lake, explore the trails in the nearby national state park, or unwind at the serene Brattleboro Common. Located about 3 miles from Chesterfield, West Chesterfield offers easy access to these attractions while providing a peaceful retreat. It's a smart choice for your next vacation stay!
Spofford
Immerse yourself in Spofford, where families and nature enthusiasts can easily access the stunning Spofford Lake, scenic mountains, and the nearby national state park. This charming city, just about 4 miles from Chesterfield, is perfect for those seeking weekend getaways or outdoor adventures, particularly during the bustling summer months from June to August. With its picturesque views and inviting atmosphere, Spofford is a smart choice for your next vacation stay.
Putney
Travelers visiting the area often choose Putney, especially those seeking a weekend getaway or outdoor adventure. This charming city offers access to beautiful Spofford Lake, the scenic expanse of a national state park, and the unique experience of Harlow's farm. With its moderate seasonal visitor numbers, Putney is ideal for family trips and nature enthusiasts alike. It’s only about a 9-mile drive from Chesterfield, making it a smart choice for your vacation.
Discover the most popular places to visit in Chesterfield
Chesterfield Hotel Deals
Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection Hotel
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91"Great welcome, nice and convenient location. Clean, quiet, updated room with a comfortable bed."
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Holiday Inn Express Hotel & Suites Brattleboro by IHG"Easy check in, clean room and nice location"
"Excellent stay. Thank you!"
Travelodge by Wyndham Brattleboro VT
Travelodge by Wyndham Brattleboro VT
Frequently Asked Questions
What are the top things to do in Chesterfield?
Chesterfield, an outdoor and nature destination, offers a variety of scenic attractions and activities for your Chesterfield vacation:
Browse and book things to do in Chesterfield on Expedia.
How can I save money on a Chesterfield vacation package?
When you bundle, you can save up to 30%*. To save money on a Chesterfield package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
Do you need to rent a car in Chesterfield, or is public transport enough?
For a Chesterfield vacation package, renting a car is highly recommended to fully explore this outdoor and nature destination. Attractions like Spofford Lake and Chesterfield Gorge Natural Area are spread out, and a car offers the flexibility to visit them at your own pace. When arriving for your Chesterfield vacation packages with flights, you'll fly into airports such as Boston, MA (BOS-Logan Intl.), Hartford, CT (BDL-Bradley Intl.), Albany, NY (ALB-Albany Intl.), Manchester, NH (MHT-Manchester-Boston Regional), or Worcester, MA (ORH-Worcester Regional), all of which require onward transportation to Chesterfield. A rental car provides the most convenient way to get around and enjoy the scenic views.
Can I change or cancel my Chesterfield vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Chesterfield vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Chesterfield vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Chesterfield?
To find last-minute vacation packages to Chesterfield, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Chesterfield vacation packages?
Free cancellation on a Chesterfield vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Chesterfield vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Chesterfield getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Chesterfield vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.