Deals on vacations and trips to Charlestown

Save when you book Charlestown package deals

Choose two or more items and save on your trip:

Charlestown flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $704, price is now $597 per person
$597
per person
Sep 18 - Sep 21
found 20 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Lebanon (LEB)
This resort features a restaurant, an outdoor tennis court, and a bar/lounge. A business center, a lobby fireplace, and a picnic area are also on offer.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,051, price is now $851 per person
$851
per person
Sep 18 - Sep 21
found 20 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
The Landgrove

The Landgrove

3.5 out of 5
Price was $756, price is now $629 per person
$629
per person
Sep 18 - Sep 21
found 20 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
This inn features a restaurant, a seasonal outdoor pool, and a bar/lounge. Families will appreciate the playground and onsite laundry facilities. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $1,053, price is now $891 per person
$891
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
This bed & breakfast features free WiFi in public areas, barbecue grills, and free self parking. A free bus station shuttle is offered as well. A 24-hour business center, a garden, and a lobby fireplace are also on offer.
Green Trails Inn

Green Trails Inn

3 out of 5
Price was $784, price is now $674 per person
$674
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Lebanon (LEB)
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A coffee shop and a garden are also provided.

Top Charlestown hotels deals

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $129 total per night
$129 total
Jul 19 - Jul 20
Total with taxes and fees
This hotel features an indoor pool and a gym. 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
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $129 total per night
$129 total
Jul 15 - Jul 16
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
1403 New Hampshire Rte 103 Newbury NH
Free Cancellation
Reserve now, pay when you stay
$153 nightly
The price is $166 total per night
$166 total
Jul 23 - Jul 24
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Bring the family and enjoy the arcade/game room, along with hiking/biking trails. There's an indoor pool on site, and a fireplace in the lobby and a communal living room are also provided.
Pool
Pet friendly
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
485 Hotel Road Brownsville VT
$154 nightly
The price is $168 total per night
$168 total
Jul 22 - Jul 23
Total with taxes and fees
This resort features a restaurant, an outdoor tennis court, and a bar/lounge. A business center, a lobby fireplace, and a picnic area are also on offer.
Restaurant
Air conditioning
Newport Motel

Newport Motel

2 out of 5
467 Sunapee St Newport NH
$107 nightly
The price is $116 total per night
$116 total
Aug 13 - Aug 14
Total with taxes and fees
Stay at this motel in Newport. Enjoy free WiFi, free parking, and housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions Wendell Marsh Wildlife Management Area and Newport Historical Society are located nearby.
Parking included
Free WiFi
Claremont Motor Lodge

Claremont Motor Lodge

2.5 out of 5
16 Beauregard St Claremont NH
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $110 total per night
$110 total
Jul 15 - Jul 16
Total with taxes and fees
Free WiFi in public areas is available at this motel. Take advantage of the free self parking.
Parking included
Free WiFi
Don't see what you're looking for?
See all available properties in Charlestown
View all properties
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.

Stay near popular Charlestown attractions

Morningside Flight Park

Walk around the campus at Morningside Flight Park during your stay in Charlestown. Discover the area's mountain views and seek out the ski slopes.
See properties

Frequently asked questions

How much are vacation packages to Charlestown?
You can pick up a great flight and hotel bundle for as low as $597. With one of our Travelocity vacation packages, a stay in Charlestown has never looked so tempting! Save some time and money and then get a start on packing those bags.
Where can I get the best vacation package deals for Charlestown?
With around 400 partner airlines and 1,000,000 properties all over the world, you can't beat Travelocity. Browse our comprehensive range and grab an affordable Charlestown package deal. Don't you love it when travel is that easy?
Why should I book my Charlestown vacation package via Travelocity?
You'll not only enjoy big savings, but you can also access our round-the-clock support, quality service and a Price Match Guarantee. Wander across the globe, uncover hidden treasures and create lifelong memories — we'll take care of the little details.
Will I save money on my Charlestown car rental if I book it with a hotel or flight?
With a Charlestown vacation package, you can bundle your hotel, flight and car bookings and save a tidy sum. When you're ready to uncover the best of this impressive city, why not make tracks to Fenway Park? This renowned attraction is 90 mi from Charlestown. With your own set of wheels, you'll be there in a jiffy.
Which airport is best for Charlestown?
Manchester-Boston Regional Airport (MHT) is 55 mi from downtown and is the beginning point for many unforgettable adventures. Alternatively, Lebanon Municipal Airport (LEB) is 25 mi away from central Charlestown and Rutland Southern Vermont Regional Airport (RUT) is 35 mi away from central Charlestown.
What is there to do in Charlestown?
Morningside Flight Park is just one of the superb sights that make Charlestown such a tourist hot spot. But allow some extra time to roam its lesser-known attractions too. This is sometimes where the best vacation memories are made.
Where should I stay when visiting Charlestown?
If you're searching for a place to base yourself, take a look at the Farmhouse on the Connecticut River. It's the top choice for many visitors.

Photos of local treasures

Browse Charlestown vacation photos for more inspiration

A grassy field with a wooden fence, surrounded by autumn-colored trees and a hill in the background.
A wooden barn with a picket fence in front.
A fenced field with trees and a building in the background.