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.
Chalet 239

Chalet 239

2 out of 5
Price was $828, price is now $652 per person
$652
per person
Aug 12 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Springfield (VSF)
The motel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. A picnic area and a virtual front desk are also provided.
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Save 100% on your flight
Price was $1,187, price is now $840 per person
$840
per person
Aug 12 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Rutland (RUT)
This hotel's 8 hot tubs and sauna are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, barbecue grills, and wedding services are also on offer.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $930, price is now $719 per person
$719
per person
Aug 12 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Springfield (VSF)
Ski-in/ski-out access, a full-service spa, and 2 hot tubs are all featured at this smoke-free resort. Enjoy a meal from the restaurant and freebies like WiFi in public areas and an area shuttle. You'll appreciate the outdoor pool, bar/lounge, and laundry facilities.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Save 100% on your flight
Price was $1,532, price is now $1,192 per person
$1,192
per person
Aug 12 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,113, price is now $900 per person
$900
per person
Aug 12 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.

Top Charlestown hotels deals

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $96 total per night
$96 total
Jun 15 - Jun 16
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and a snack bar/deli and a picnic area are also provided.
Breakfast included
Pet friendly
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
$160 nightly
The price is $174 total per night
$174 total
Jun 14 - Jun 15
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
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
Jun 14 - Jun 15
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
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
Free Cancellation
$144 nightly
The price is $157 total per night
$157 total
Jun 15 - Jun 16
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
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $133 total per night
$133 total
Jun 14 - Jun 15
Total with taxes and fees
Free self parking is available and the motel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A picnic area is also provided.
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
Jun 16 - Jun 17
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.

Popular places to visit

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.

Morningside Flight Park

Charlestown Town Hall

After visiting Charlestown Town Hall, make a plan to see the other sights and activities in Charlestown. Take in the museums while you're in the area.

Charlestown Town Hall

Connecticut River State Park

Explore the great outdoors at Connecticut River State Park, a lovely green space in Charlestown. Take in the museums while you're in the area.

Connecticut River State Park

Frequently asked questions

How much are vacation packages to Charlestown?
You can pick up a great flight and hotel bundle for as low as $652. 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

View from the Fort Tower
Fort #4 - Parker House
Fort # 4 NW Corner