A grassy field with a wooden fence, surrounded by autumn-colored trees and a hill in the background.

Charlestown Vacation Rentals

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Our top choices for Charlestown vacation rentals

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 slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
The price is CA $86
CA $348 total
includes taxes & fees
Jul 6 - Jul 7
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Hideaway Cottages, Cottage B

Hideaway Cottages, Cottage B
New London
10.0 out of 10, Exceptional, (38 reviews)
"Character-filled old NH cabin nicely located on beautiful setting close to amenities"
United States
Brian
The price is CA $287
CA $427 total
includes taxes & fees
Jul 14 - Jul 15
Hideaway Cottages, Cottage B

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
Jul 6 - Jul 7
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Hideaway Cottages, Cottage A

Hideaway Cottages, Cottage A
New London
9.6 out of 10, Exceptional, (63 reviews)
"Awesome placeThe host was attentive to every needWould highly recommend"
United States
paul K.
The price is CA $231
CA $357 total
includes taxes & fees
Jul 7 - Jul 8
Hideaway Cottages, Cottage A

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 $524 total
includes taxes & fees
Jul 8 - Jul 9
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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 $228
CA $675 total
includes taxes & fees
Jul 6 - Jul 7
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location, "
United States
Bryan R J.
The price is CA $177
CA $382 total
includes taxes & fees
Jul 7 - Jul 8
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is CA $142
CA $326 total
includes taxes & fees
Jul 7 - Jul 8
Efficient condo near slopes with kitchenette & great location

Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
The price is CA $142
CA $334 total
includes taxes & fees
Jul 7 - Jul 8
Cozy Studio Condo with Great Location, WiFi & Kitchenette

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 $287
CA $544 total
includes taxes & fees
Jul 11 - Jul 12
Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
The price is CA $311
CA $715 total
includes taxes & fees
Jul 6 - Jul 7
Cozy Private Cabin in Andover - Fireplace & Hot tub

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is CA $149
CA $372 total
includes taxes & fees
Jul 7 - Jul 8
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

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 $125
CA $476 total
includes taxes & fees
Aug 1 - Aug 2
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

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 6 - Jul 7
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

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 $258
CA $465 total
includes taxes & fees
Jul 8 - Jul 9
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
Ludlow
8.0 out of 10, Very good, (3 reviews)
"The cabin was very clean and offered everything we needed for our ski vacation! Access to the ski mountain was very close which was great! "
United States
Anne W.
The price is CA $325
CA $662 total
includes taxes & fees
Jul 6 - Jul 7
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 $242
CA $463 total
includes taxes & fees
Jul 9 - Jul 10
Brook Road Cabin

Okemo's Back Room - in the heart of the village on the shuttle route!

Okemo's Back Room - in the heart of the village on the shuttle route!
Ludlow
9.6 out of 10, Exceptional, (15 reviews)
"Cool building, right on main street. Building is undergoing renovation on back porches so some construction material and disruption. The kitchen was not well equiped and needs an update. However, the space is really cool, very open, big bedrooms, decent bedding. Shower is a little small but nice. Good value"
United States
jonathan w.
The price is CA $230
CA $574 total
includes taxes & fees
Jul 9 - Jul 10
Okemo's Back Room - in the heart of the village on the shuttle route!

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is CA $319
CA $863 total
includes taxes & fees
Jul 6 - Jul 7
Terrific 3-bedroom cottage with AC in charming Cavendish
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?

HISTORIC, RENOVATED BARN w/ Mt. SUNAPEE VIEW, SLEEPS 22+, Minutes to Lake / Mt.: This vacation home rental near Charlestown is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a library.

What’s there to see and do in Charlestown?

Connecticut River and Connecticut River State Park 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.