Chesterfield Vacations from $491
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The Latest Chesterfield Vacation Packages
- Stonybrook Motel & Lodge
Sep 3 - Sep 7Stonybrook Motel & Lodge + Flight
Franconia4 nights2.0 star property7.6/10 - Good (1,003 reviews)Roundtrip • Baltimore (BWI) - Manchester (MHT)BWI - MHT • Nonstop MHT - BWI • Nonstop - The Village of Loon Mountain Fixed Rooms
Sep 3 - Sep 7The Village of Loon Mountain Fixed Rooms + Flight
Lincoln4 nights2.0 star property8.6/10 - Excellent (59 reviews)"There was not adequate parking. The indoor and outdoor pools were freezing with the exception of one, but that one was loaded with children. The paint was peeling everywhere. There were much needed repairs visible in the room, as well as in the pool area. The hotel only allowed one pool towel. The room had a fireplace that did not work and a toaster that also did not work. We would never recommend this place."Reviewed July 22, 2026Roundtrip • Baltimore (BWI) - Manchester (MHT)BWI - MHT • Nonstop MHT - BWI • Nonstop - The Village of Loon Mountain
Sep 3 - Sep 7The Village of Loon Mountain + Flight
Lincoln4 nights3.0 star property8.6/10 - Excellent (591 reviews)Roundtrip • Baltimore (BWI) - Manchester (MHT)BWI - MHT • Nonstop MHT - BWI • Nonstop - Bluegreen Vacations South Mountain, an Ascend Collection Resort
Sep 3 - Sep 7Bluegreen Vacations South Mountain, an Ascend Collection Resort + Flight
Lincoln4 nights3.0 star property9.2/10 - Wonderful (645 reviews)Roundtrip • Baltimore (BWI) - Manchester (MHT)BWI - MHT • Nonstop MHT - BWI • Nonstop$667$511found 6 hours agoper traveler - Omni Bretton Arms Inn at Mount Washington
Sep 3 - Sep 7Omni Bretton Arms Inn at Mount Washington + Flight
Bretton Woods4 nights4.0 star property9.0/10 - Wonderful (508 reviews)"An oasis among the bigger Omni hotel All the perks but away from the bustle"Reviewed July 22, 2026Roundtrip • Baltimore (BWI) - Manchester (MHT)BWI - MHT • Nonstop MHT - BWI • Nonstop
Chesterfield Hotel Deals
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91
Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection Hotel
Frequently Asked Questions
How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this top destination from $491 on Expedia. However, how much your vacation to Chesterfield costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Chesterfield?
If you'd like to snag a cheap Chesterfield vacation package, consider visiting in October, November and December. You'll typically find lower prices on flights and accommodations during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Chesterfield?
With a well-planned schedule, you can easily hit the main Chesterfield sights in a few days. But if you prefer to discover hidden gems or take day trips, consider booking your Chesterfield vacation for longer.
How to find the best Chesterfield package deals?
Use Expedia's filter tool to find some terrific Chesterfield package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Chesterfield package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Chesterfield vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still have the freedom to create a personalized Chesterfield vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Chesterfield?
If you're considering a spur-of-the-moment Chesterfield adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
Your Chesterfield trip should be a relaxing escape from your busy life, not a source of money worries. So to give you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.