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.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $719, price is now $639 per person
$639
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Springfield (VSF)
This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast and free WiFi. A garden and a picnic area are also provided.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $1,277, price is now $1,067 per person
$1,067
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Lebanon (LEB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. A grocery/convenience store, a computer station, and laundry facilities are also on offer.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $936, price is now $800 per person
$800
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) 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 Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $928, price is now $822 per person
$822
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) 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.
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $957, price is now $850 per person
$850
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Rutland (RUT)
A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury hotel. Enjoy the indoor pool and perks like free self parking and free WiFi. You'll appreciate the gym, bar/lounge, and concierge services.

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
$129 nightly
The price is $140 total per night
$140 total
Jul 23 - Jul 24
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
$139 nightly
The price is $151 total per night
$151 total
Jul 23 - Jul 24
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
$93 nightly
The price is $101 total per night
$101 total
Jul 26 - Jul 27
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.
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
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
$125 nightly
The price is $136 total per night
$136 total
Jul 29 - Jul 30
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.
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 20 - Aug 21
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 Lake Sunapee and Wendell Marsh Wildlife Management Area are located nearby.
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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.

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.
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Frequently asked questions

How much are vacation packages to Charlestown?
You can pick up a great flight and hotel bundle for as low as $639. 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.