Charlestown Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Charlestown vacation rentals

Outdoor dining

Hideaway Cottages, Cottage A

Hideaway Cottages, Cottage A
New London
9.6 out of 10, Exceptional, (58 reviews)
"Awesome placeThe host was attentive to every needWould highly recommend"
United States
paul K.
The price is ￥21,152
￥33,151 total
includes taxes & fees
May 20 - May 21
Hideaway Cottages, Cottage A
Fridge, microwave, oven, stovetop

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (57 reviews)
"everything was perfect "
United States
Stephen C.
The price is ￥29,002
￥64,043 total
includes taxes & fees
May 14 - May 15
Chic Farmhouse Decor | Deck w/View
TV

Hideaway Cottages, Cottage B

Hideaway Cottages, Cottage B
New London
10.0 out of 10, Exceptional, (34 reviews)
"Character-filled old NH cabin nicely located on beautiful setting close to amenities"
United States
Brian
The price is ￥22,069
￥35,031 total
includes taxes & fees
May 18 - May 19
Hideaway Cottages, Cottage B
Exterior

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)
"3rd year at this listing, absolutely love it. Close to okemo and mount snow. Host got back to me very quickly when reached out to. "
United States
Jake D.
The price is ￥26,636
￥56,330 total
includes taxes & fees
May 20 - May 21
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior

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, (18 reviews)
"It was an amazing experience! "
United States
Gruha
The price is ￥24,757
￥45,503 total
includes taxes & fees
May 13 - May 14
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Exterior

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is ￥25,936
￥45,949 total
includes taxes & fees
May 18 - May 19
Wellness Getaway with a Personal Sauna, and Private River Beach!
TV

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)
"Location location location!"
United States
Britt H.
The price is ￥19,649
￥65,544 total
includes taxes & fees
May 13 - May 14
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Exterior detail

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (15 reviews)
"Location was great"
United States
Andrew P.
The price is ￥26,636
￥50,660 total
includes taxes & fees
May 20 - May 21
Brook Road Condo
Exterior

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
Newbury
10.0 out of 10, Exceptional, (30 reviews)
"Amazing property! Would definitely stay here again "
New Zealand
Jackie M.
The price is ￥38,778
￥71,145 total
includes taxes & fees
May 13 - May 14
Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
Exterior

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.8 out of 10, Exceptional, (22 reviews)
"Amazing weekend stay with our pup! Looking forward to staying here in the summer! "
United States
Naydene G.
The price is ￥28,294
￥58,500 total
includes taxes & fees
May 13 - May 14
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Property grounds

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
9.0 out of 10, Wonderful, (80 reviews)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
The price is ￥11,789
￥40,776 total
includes taxes & fees
May 16 - May 17
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Newbury
10.0 out of 10, Exceptional, (20 reviews)
"Our host went above and beyond to make our experience memorable. The house was very clean and we had a nice bottle of wine and snacks waiting for us. This house is close to the mountain and right near the lake. We will rent here again "
United States
Walter B.
The price is ￥29,613
￥71,061 total
includes taxes & fees
May 18 - May 19
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (21 reviews)
"Great time easy to get to clean quiet and peaceful definitely would recommend for romantic getaway "
United States
Garrett B.
The price is ￥43,227
￥53,383 total
includes taxes & fees
May 17 - May 18
Owl's Nest Treehouse
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is ￥25,606
￥47,165 total
includes taxes & fees
May 13 - May 14
Family Friendly Hilltop House In Putney Vermont
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is ￥35,187
￥41,930 total
includes taxes & fees
May 13 - May 14
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Interior

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (56 reviews)
"The place was very dirty. The linens were dirty, the pots/pans and all of the cooking utensils were dirty. There was a rubber band on the floor in bathroom that didn't belong to us.There was only 3 forks and a few spoons. Very little silverwear."
United States
Leigh-Ellen F.
The price is ￥18,802
￥59,799 total
includes taxes & fees
May 17 - May 18
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Property grounds

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)
"Great property, clean and close to the slope"
United States
tiliger01
The price is ￥7,702
￥35,031 total
includes taxes & fees
May 13 - May 14
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Family Cabin, 2 Bedrooms, Mountain View | Living room | 40-inch Smart TV with cable channels, TV, Netflix

Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.8 out of 10, Good, (9 reviews)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
The price is ￥28,767
￥46,852 total
includes taxes & fees
May 18 - May 19
Brook Road Cabin
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is ￥17,684
￥47,674 total
includes taxes & fees
May 13 - May 14
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Interior

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Clock Tower Base Area
9.4 out of 10, Exceptional, (27 reviews)
"This condo is a true ski-in, ski-out experience! Literally walked out the back door and skied to the lift. (A/B lifts) The kitchen was well appointed, the bed comfortable, and was perfectly set up for a ski vacation. The entire space had a comfortable, rustic vibe. Would definitely stay here again when returning to Okemo."
United States
Patricia D.
The price is ￥23,579
￥60,558 total
includes taxes & fees
May 13 - May 14
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Very clean. Well equipped kitchen. Helpful staff."
Pamela 2-night trip
Posted 4 hours ago
Pointe at Castle Hill Resort

Find out more about Charlestown

Search for holiday rentals in Charlestown on Expedia! You can easily find your home rentals, villas, holiday apartments in Charlestown using one of the methods below:

  • View our selection of featured holiday rentals in Charlestown
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Look no further and take a look at our great range of rental properties in Charlestown!

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?

Spacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat: You might like this vacation home rental near Charlestown. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Silsby Free Public Library 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.