Chesterfield Vacations from $525

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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

Price found within the past 48 hours. Click for updated prices.
Stonybrook Motel & Lodge

Stonybrook Motel & Lodge

2 out of 5
Price was $729, price is now $525 per person
$525
per person
Sep 3 - Sep 7
just found
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
7.6/10 Good! (1,003 reviews)
Cozy super old fashioned little motel with a lock and key. Actually loved it here, perfect area and close to everywhere I planned to hike. Definitely would stay here again. Super affordable and the dude at the front desk was super cool

Reviewed on Jun 22, 2026

The Lake Estate on Winnisquam

The Lake Estate on Winnisquam

4.5 out of 5
Save 100% on your flight
Price was $1,856, price is now $1,222 per person
$1,222
per person
Sep 3 - Sep 7
just found
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
9.8/10 Exceptional! (35 reviews)
The property was beautiful, exceptionally well-maintained, and spotless throughout. From the lobby to the guest rooms, everything was clean, comfortable, and thoughtfully cared for. The staff was friendly and welcoming, which made our experience even better. It was clear that great attention is given to both the appearance and upkeep of the hotel. We would gladly stay here again and highly recommend it to others looking for a relaxing and enjoyable stay

Reviewed on Jun 24, 2026

Mountain View Grand Resort & Spa

Mountain View Grand Resort & Spa

4 out of 5
Save 100% on your flight
Price was $1,004, price is now $728 per person
$728
per person
Sep 3 - Sep 7
just found
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
8.8/10 Excellent! (1,000 reviews)
Very nice place clean,friendly

Reviewed on Jun 24, 2026

Eagle Mountain House & Golf Club

Eagle Mountain House & Golf Club

3.5 out of 5
Price was $838, price is now $641 per person
$641
per person
Sep 3 - Sep 7
just found
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
8.8/10 Excellent! (1,001 reviews)
The hotel is historical and rooms reflect that. The staff are friendly and very welcoming! The grounds are beautiful and the location is perfect! The bar onsite is fantastic and enjoying a beverage on the porch is magical. Beautiful place!

Reviewed on Jun 21, 2026

The Village of Loon Mountain

The Village of Loon Mountain

3 out of 5
Price was $796, price is now $632 per person
$632
per person
Sep 3 - Sep 7
just found
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
8.6/10 Excellent! (579 reviews)
The place was very nice, very clean, spacious, excellent pools, gym, grill, playground for the kids. Everything great. Just a brown young lady whose host the pool side and gym she should be more polite and sweet with the guest specially with kids. Except it. Everything was great.

Reviewed on Jun 21, 2026

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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.
See properties

Chesterfield Hotel Deals

Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $127 total per night from Jul 5 to Jul 6
$127 total
Jul 5 - Jul 6
Total with taxes and fees
8.6/10 Excellent! (910 reviews)
"No air conditioning in room. Funky historic place with a lot of charm. It’s part of the same non-profit as the theater next door so a pretty unconventional hospitality experience."

Reviewed on Jun 26, 2026

Latchis Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $129 total per night from Jun 28 to Jun 29
$129 total
Jun 28 - Jun 29
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
"Everything was great except that the room's bathroom floor was still wet, presumably from the previous occupant."

Reviewed on Jun 25, 2026

Best Western Plus Keene Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $126 total per night from Jul 2 to Jul 3
$126 total
Jul 2 - Jul 3
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"Other than the night paving project taking place outside the hotel, the stay was okay. The hotel is not responsible for the timing of the project, but it might be mindful to assign rooms furthest from the main drag."

Reviewed on Jun 26, 2026

Hampton Inn Brattleboro
See all 523 properties in Chesterfield
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.

Find the Best Chesterfield Vacation Packages

Chesterfield Essential Information

Language
English
Currency
U.S dollars
Population
3,800
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Colonial Theatre, Pisgah State Park and Cheshire Childrens Museum

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Frequently asked questions

How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this top destination from $525 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.