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.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $1,011, price is now $816 per person
$816
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Springfield (VSF)
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.
The Landgrove

The Landgrove

3.5 out of 5
Save 100% on your flight
Price was $1,349, price is now $838 per person
$838
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $1,384, price is now $1,079 per person
$1,079
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,134, price is now $915 per person
$915
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was $1,022, price is now $826 per person
$826
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Rutland (RUT)
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.

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
$330 nightly
The price is $358 total per night
$358 total
Oct 2 - Oct 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
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
Free Cancellation
Reserve now, pay when you stay
$183 nightly
The price is $201 total per night
$201 total
Sep 30 - Oct 1
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
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
$142 nightly
The price is $155 total per night
$155 total
Sep 9 - Sep 10
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
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
$145 nightly
The price is $158 total per night
$158 total
Oct 1 - Oct 2
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
Claremont Motor Lodge

Claremont Motor Lodge

2.5 out of 5
16 Beauregard St Claremont NH
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $128 total per night
$128 total
Sep 10 - Sep 11
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
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$128 nightly
The price is $139 total per night
$139 total
Sep 13 - Sep 14
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
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 $816. 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.