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 Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Price was $487, price is now $410 per person
$410
per person
Jun 24 - Jun 26
found 2 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Rutland (RUT)
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,526, price is now $1,336 per person
$1,336
per person
Jun 23 - Jun 26
found 2 hours ago
Roundtrip flight included
Denver (DEN) to Springfield (VSF)
This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $984, price is now $896 per person
$896
per person
Jun 23 - Jun 26
found 2 hours ago
Roundtrip flight included
Denver (DEN) 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.
Chateau Rooms

Chateau Rooms

4.5 out of 5
Price was $1,108, price is now $1,009 per person
$1,009
per person
Jun 23 - Jun 26
found 2 hours ago
Roundtrip flight included
Denver (DEN) to Rutland (RUT)
This smoke-free guesthouse features a full-service spa and a restaurant. A convenience store and wedding services are also provided.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $542, price is now $456 per person
$456
per person
Jun 24 - Jun 26
found 2 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Rutland (RUT)
A private beach and a restaurant are featured at this smoke-free lodge. Enjoy the seasonal outdoor pool and perks like free self parking. There's a bar/lounge on site, and a terrace and barbecue grills are also provided.

Top Charlestown hotels deals

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
$154 nightly
The price is $167 total per night
$167 total
May 10 - May 11
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
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$140 nightly
The price is $152 total per night
$152 total
May 20 - May 21
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.
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
$140 nightly
The price is $152 total per night
$152 total
May 26 - May 27
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
Free Cancellation
$164 nightly
The price is $179 total per night
$179 total
May 10 - May 11
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.
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
May 11 - May 12
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.
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
$105 nightly
The price is $115 total per night
$115 total
May 10 - May 11
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
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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

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

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

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

Frequently asked questions

How much are vacation packages to Charlestown?
You can pick up a great flight and hotel bundle for as low as $410. 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