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!

Charlestown Chalets

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Our total price for your stay includes taxes and fees

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Chalets in Charlestown

Stunning hallway with carpeted floor, wooden staircase, and panelled walls.

"A terrific place. Highly recommended. We had a great family ski vacation."

$1,768 nightly

Aug 10 - Aug 11

Total includes taxes and fees

Enjoy cooking in this warm kitchen with a large island and dishwasher, surrounded by natural light and a view of the landscape.

"Girls family weekend, relaxing, visiting and enjoying the hot tub."

Escape to a serene forest retreat with a cozy cabin featuring a charming front porch and balcony overlooking the surrounding trees.

"We spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."

$392 nightly

Sep 5 - Sep 6

Total includes taxes and fees

"Excellent week at a cozy property, convenient to Killington and Okemo. Easy check in and check out; highly responsive and helpful host. Would recommend to those looking for a great VT escape."

$435 nightly

Sep 1 - Sep 2

Total includes taxes and fees

Enjoy cooking in this kitchen with a central island, bar stools, stainless steel appliances, and a large window offering a view of the outdoors.

"Roshanak was an excellent host and the place is beautiful. We love the location and its proximity to Okemo and the town. The property is gorgeous, we would book again."

Relax in a serene forest setting with a fire pit and Adirondack chair.

"We found the hosts to be super helpful and friendly. Location was fantastic. We loved the hot tub and wood burning stove. It was a perfect stay for my extended family and I. The beds were also super comfortable-we slept great! We would definitely recommend this spot!"

Relax in this inviting living room with a comfortable sofa and large glass doors leading to an outdoor area.

"Loved the location and the house was great. All amenities were as described. Great host. Highly recommend. "

Enjoy cooking in this kitchen with a sleek countertop, stainless steel appliances, and white cabinetry, offering a view of the outdoors.

"Very large, bright and completely remodeled. Plenty of space for a large family to hang out in the kitchen area and living room."

$553 nightly

Aug 10 - Aug 11

Total includes taxes and fees

"My family loved our stay. Would strongly recommend!"

Enjoy al fresco dining and grilling on this deck overlooking the forest.

"A wonderful and spacious house that is perfect for large groups. The house was well stocked, host was responsive and helpful, and the hot tub was great! Would definitely stay here again. "

Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, microwave, and dishwasher.

"We had a fabulous stay here. Owner was v communicative and accommodating."

Guests can enjoy a covered porch with large windows and a beautiful winter view.

"We were up for a weekend in February. Perfect place. Plenty of beds. The hot tub was a bonus. Excellent communication by the hosts. "

Relax in this stylish living room with a fireplace, leather sofa, and a window offering a view of the outdoors.

Relax in this serene bedroom with a large bed, ceiling fan, and flat-screen TV.

"Great house, made our ski weekend easy and fun. House is better than the pictures."

Enjoy the view from the upper-level balcony with a large arched window and a railing.

"This is our second year staying at this beautiful home. We love the space and amenities, not to mention the location to the mountain. The owners have been very accommodating and communicative. Overall, a wonderful stay for our group of families and hope to return again when we come back to Ludlow."

Escape to a cozy cabin surrounded by a forest, with a balcony offering a peaceful retreat.

"This was our second time staying at the Bear Chalet and we absolutely loved it. So much space for multiple families and very kid friendly!"

Enjoy a tranquil moment on the deck with a potted plant and comfortable seating.

"Great, well kept and supplied house. Had a great ski weekend. Great kitchen and family area."

Relax by the fire pit surrounded by Adirondack chairs in a serene natural setting.

"We had a great stay here! The host was very informative and pleasant to work with and the house offered a lot of amenities. Lots of beds which is perfect for a big group. Thank you for hosting us!"

Relax in this open-plan living area with a central island, gas stove, and comfortable seating.

"The house was wonderful. House was clean. Our family had a wonderful time playing in the backyard. Close to numerous ski towns. The bunkbed downstairs was a nice surprise."