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Charlestown Vacation Rentals

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Our top choices for Charlestown vacation rentals

Hideaway Cottages, Cottage A

Hideaway Cottages, Cottage A
New London
9.6 out of 10, Exceptional, (62 reviews)
"Awesome placeThe host was attentive to every needWould highly recommend"
United States
paul K.
The price is CA $280
CA $413 total
includes taxes & fees
Jul 22 - Jul 23
Hideaway Cottages, Cottage A

Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (18 reviews)
"We had a great stay! Cabin is cozy and met all of our needs for the weekend. We loved exploring the nearby trails and shops. Our dogs loved it as well :) "
United States
Kelsey M.
Hiking Trails On-Site: Cozy Falls Brook Cabin

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (19 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is CA $235
CA $425 total
includes taxes & fees
Jun 29 - Jun 30
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (169 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is CA $241
CA $523 total
includes taxes & fees
Jul 27 - Jul 28
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
Hiking Trails On-site: Cozy Falls Brook Cabin

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"Our stay was perfectly pleasant but the parking was far from the unit and the ski school and daycare was on a different part of the mountain which made the location inconvenient for having little kids with us."
United States
Teresa W.
The price is CA $106
CA $378 total
includes taxes & fees
Jun 30 - Jul 1
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Hideaway Cottages, Cottage B

Hideaway Cottages, Cottage B
New London
10.0 out of 10, Exceptional, (37 reviews)
"Character-filled old NH cabin nicely located on beautiful setting close to amenities"
United States
Brian
The price is CA $287
CA $426 total
includes taxes & fees
Jun 28 - Jun 29
Hideaway Cottages, Cottage B

•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area

•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area
Sutton
10.0 out of 10, Exceptional, (19 reviews)
"Host was extremely welcoming and the place was great."
United States
Chad C.
The price is CA $256
CA $581 total
includes taxes & fees
Jul 8 - Jul 9
•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
The price is CA $73
CA $326 total
includes taxes & fees
Jun 28 - Jun 29
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
The price is CA $311
CA $712 total
includes taxes & fees
Jun 28 - Jun 29
Cozy Private Cabin in Andover - Fireplace & Hot tub

Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee

Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
Sunapee
10.0 out of 10, Exceptional, (58 reviews)
"Wonderful place to stay for our trip. Great location and the house was nicely updated. "
United States
Andrew W.
The price is CA $432
CA $799 total
includes taxes & fees
Jul 22 - Jul 23
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee

Magic Mountain Trailside Condo - Ski In / Ski Out

Magic Mountain Trailside Condo - Ski In / Ski Out
Londonderry
9.8 out of 10, Exceptional, (14 reviews)
"Nice and we enjoyed our stay"
United States
Gretchen H.
The price is CA $177
CA $447 total
includes taxes & fees
Jun 30 - Jul 1
Magic Mountain Trailside Condo - Ski In / Ski Out

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
Townshend
8.0 out of 10, Very good, (1 review)
"Very nice place, an ideal VT cabin!"
United States
David D.
The price is CA $230
CA $474 total
includes taxes & fees
Jun 29 - Jun 30
Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Very clean and comfortable for our family of 4. Great ski-in/ski-out location - easily accessible to all lifts. Highly recommend. "
United States
Carey S.
The price is CA $186
CA $611 total
includes taxes & fees
Jun 28 - Jun 29
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Ludlow
8.6 out of 10, Excellent, (4 reviews)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
The price is CA $142
CA $366 total
includes taxes & fees
Jun 30 - Jul 1
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
The price is CA $164
CA $533 total
includes taxes & fees
Jul 1 - Jul 2
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Well-appointed studio right downtown - less than a mile to Okemo Mountain

Well-appointed studio right downtown - less than a mile to Okemo Mountain
Ludlow
8.8 out of 10, Excellent, (13 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is CA $142
CA $438 total
includes taxes & fees
Jun 30 - Jul 1
Well-appointed studio right downtown - less than a mile to Okemo Mountain

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (61 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is CA $254
CA $460 total
includes taxes & fees
Jul 1 - Jul 2
Family Friendly Hilltop House In Putney Vermont

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is CA $403
CA $634 total
includes taxes & fees
Jul 17 - Jul 18
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17 reviews)
"Would go back!"
United States
Elizabeth C.
The price is CA $241
CA $462 total
includes taxes & fees
Jun 29 - Jun 30
Brook Road Cabin
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.
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Top Charlestown Hotel Reviews

Find out more about Charlestown

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Charlestown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Charlestown?

Yes, we offer vacation rentals close to the most popular sights in Charlestown, or you can go with a more remote option if you want a relaxing place to stay. Charlestown is known for its university setting and museums.

What are some of the best vacation rentals that Charlestown has to offer?

Mountainside 5-BR Ski-In/Out Okemo Villa: This vacation home near Charlestown is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a hot tub.

What’s there to see and do in Charlestown?

Connecticut River and Glidden Island are a couple of scenic spots to enjoy the outdoors, whereas The Fort at No.4 Open Air Museum is one of the cultural attractions. Charlestown Town Hall and Spaulding Wildlife Management Area are other places to visit while you're in town.

What’s a vacation rental in Charlestown like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Charlestown. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.