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 Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $968, price is now $798 per person
$798
per person
Mar 15 - Mar 19
found 2 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Rutland (RUT)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free ski shuttle and onsite ski storage. Enjoy the gym and free perks like continental breakfast and free self parking.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $1,763, price is now $1,209 per person
$1,209
per person
Mar 15 - Mar 19
found 2 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Rutland (RUT)
An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Save 100% on your flight
Price was $1,586, price is now $1,178 per person
$1,178
per person
Mar 15 - Mar 19
found 2 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Rutland (RUT)
An outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. Concierge services and a virtual front desk are also provided.
Hanover Inn Dartmouth

Hanover Inn Dartmouth

4 out of 5
Price was $1,708, price is now $1,397 per person
$1,397
per person
Mar 7 - Mar 13
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Lebanon (LEB)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, a lobby fireplace, and a computer station are also on offer.
Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Price was $3,734, price is now $3,093 per person
$3,093
per person
Mar 7 - Mar 13
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Rutland (RUT)
This vacation home features laundry facilities. Take advantage of the free self parking.

Top Charlestown hotels deals

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$161 nightly
The price is $175 total per night
$175 total
Jan 14 - Jan 15
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
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
$144 nightly
The price is $156 total per night
$156 total
Jan 19 - Jan 20
Total with taxes and fees
An indoor pool, free self parking, and a virtual front desk are featured at this hotel. WiFi in public areas is free. A lobby fireplace, a communal living room, and express check-out are also on offer.
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
Free Cancellation
$164 nightly
The price is $179 total per night
$179 total
Feb 8 - Feb 9
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
Jackson Gore Village

Jackson Gore Village

3 out of 5
111 Jackson Gore Road Ludlow VT
$431 nightly
The price is $474 total per night
$474 total
Jan 22 - Jan 23
Total with taxes and fees
Ski-in/ski-out access, 2 restaurants, and 3 hot tubs are all featured at this smoke-free hotel. 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
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
$79 nightly
The price is $87 total per night
$87 total
Jan 12 - Jan 13
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.
Breakfast included
Pet friendly
Best Western Springfield Hotel

Best Western Springfield Hotel

2.5 out of 5
818 Charlestown Rd Springfield VT
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $167 total per night
$167 total
Jan 19 - Jan 20
Total with taxes and fees
This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A safe deposit box and laundry facilities are also provided.
Pool
Breakfast included
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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

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 $798. 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