Deals on vacations and trips to Charlestown

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Charlestown flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $818, price is now $695 per person
$695
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Springfield (VSF)
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Save 100% on your flight
Price was $2,894, price is now $2,374 per person
$2,374
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Rutland (RUT)
This cabin doesn't skimp on freebies - guests receive free WiFi and free self parking. Enjoy ski-in/ski-out access and onsite ski storage. Enjoy the sauna and conveniences like express check-out and laundry facilities.
Beechwood Home in Mendon

Beechwood Home in Mendon

2 out of 5
Save 100% on your flight
Price was $3,784, price is now $3,127 per person
$3,127
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Rutland (RUT)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities are provided for your convenience.
Sweet Life in Pittsfield

Sweet Life in Pittsfield

2 out of 5
Save 100% on your flight
Price was $3,050, price is now $2,549 per person
$2,549
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Rutland (RUT)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A full-service spa is also provided.
The Engel House

The Engel House

3 out of 5
Price was $881, price is now $754 per person
$754
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Rutland (RUT)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free buffet breakfast each morning. A lobby fireplace, a communal living room, and a library are also on offer.

Top Charlestown hotels deals

Jackson Gore Village

Jackson Gore Village

3 out of 5
111 Jackson Gore Road, Ludlow, VT
$193 nightly
The price is $213 total per night
$213 total
Nov 6 - Nov 7
Total with taxes and fees
This smoke-free hotel features ski-in/ski-out access, a full-service spa, and 2 restaurants. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.
Pool
Hot Tub
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
$107 nightly
The price is $116 total per night
$116 total
Nov 2 - Nov 3
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
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
$182 nightly
The price is $198 total per night
$198 total
Nov 2 - Nov 3
Total with taxes and fees
This resort features a restaurant, an indoor pool, and a bar/lounge. There's an outdoor tennis court on site, and a fireplace in the lobby and a picnic area are also provided.
Pool
Restaurant
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103, Cavendish, VT
$136 nightly
The price is $148 total per night
$148 total
Nov 3 - Nov 4
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St, Keene, NH
$140 nightly
The price is $152 total per night
$152 total
Nov 3 - Nov 4
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
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
$101 nightly
The price is $110 total per night
$110 total
Nov 4 - Nov 5
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
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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

Hang gliding with Morningside Flight Park! AMAZING! For $175, you will be strapped into a tandem hang-glider and towed up for a 10-minute flight over the Connecticut River Valley. Your instructor will do all the work if you'd rather, OR they will let you try controlling the aircraft while you're drifting through the air!

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

The Fort at No.4 Open Air Museum

You can spend an afternoon exploring the galleries in The Fort at No.4 Open Air Museum during your trip to Charlestown. Wander the riverfront or discover the area's stargazing spots.

The Fort at No.4 Open Air Museum

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

Frequently asked questions

How much are vacation packages to Charlestown?
You can pick up a great flight and hotel bundle for as low as $695. 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

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Photo by The Curious Zephyr
Photo by The Curious Zephyr