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Top Holiday Rentals in Charlestown

Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (30)
"My family really enjoyed this Lake House. The beautiful views of the lake were breathtaking. The house had everything we needed for preparing meals. The kitchen was functional and generally well equipped. The beds in the house were particularly comfortable. We enjoyed early morning coffee on the deck with perfect views of the lake. The location was great. Lots of wonderful hiking trials in close proximity. My only suggestion to the owners is to give the house a good deep cleaning. Nonetheless,...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
1 bedroom, Internet
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (9)
"This is an adorable spot! Super quiet, the treehouse is very unique, and moments away from downtown Woodstock. We’ll be back!"
The price is £149
includes taxes & fees
20 May - 21 May
Treehouse at Wise Pines- SoBo
Exterior
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
9.8 out of 10, Exceptional, (157)
"The place is beautiful and the stay was fantastic. It is up a couple mile hill/road from the center of town, just long enough to make you feel you are out of the hustle. The property presents very well. The rooms are large for private space with 2 common rooms that are just as large for group time. The one suggestion would be to add a check in book of information, including necessary passwords (WIFI) and local attractions/restaurants. We had much of this in the interaction with the host through...
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
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Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (140)
"Great little house to enjoy spending time with family and all that VT has to offer. Wonderful host, we will be back."
The price is £289
includes taxes & fees
20 May - 21 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
6 bedrooms, WiFi, bed sheets
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
9.6 out of 10, Exceptional, (69)
"This was our second stay at the condo. Can’t beat the convenience of ski in ski out and coming home for lunch. The owner, Ralph, is very quick at getting back with any questions. Highly recommend!"
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
Fridge, microwave, oven, stovetop
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
9.8 out of 10, Exceptional, (15)
"Great location to restaurant and ski mountain"
The price is £233
includes taxes & fees
19 May - 20 May
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Property grounds
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (141)
"Ursula was super helpful and the location is very charming. Perfect spot for us!"
The price is £413
includes taxes & fees
1 Jun - 2 Jun
Idyllic Lakefront House Suited Two Families
Lake
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
10.0 out of 10, Exceptional, (116)
"Great place to stay for an early spring ski trip and eclipse viewing (we drove north after checking out). Clean, cozy place and pet friendly for our small dog. Located on a quiet dirt road but close to Ludlow town center and Okemo for skiing. Not too far from Killington either (which is where we went to ski). Minor issue for me was the bed was a bit too soft for my liking but otherwise, great place and would consider again in future."
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Fridge, microwave, oven, stovetop
Lakefront home with amazing views, fireplace, firepit, & gas grill
9.8 out of 10, Exceptional, (58)
"Awesome house. Great location. I would stay there again for sure!"
Lakefront home with amazing views, fireplace, firepit, & gas grill
Property grounds
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (187)
"We had a lovely stay, the kayaks and canoe were the feature of one afternoon and we greatly enjoyed paddling around Lake Pauline and checking out both dam areas. The house is very clean and well maintained, we fell in love with all the windows and light coming in the bedroom across from the bathroom. The quick walk to the sugar house was a feature for my kids, they also loved having the wii in their room and playing Mario kart with their aunt/uncle."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Property grounds
Rustic Big Red Cottage near Sunapee
9.8 out of 10, Exceptional, (10)
"We had a lovely stay at the Big Red cottage. The home is modern and beautifully furnished and in a serene wooded setting. Everything went very smoothly and we very much enjoyed relaxing both inside and out on a Sunapee ski weekend. I highly recommend the home and hope to stay there again soon."
Rustic Big Red Cottage near Sunapee
Fridge, microwave, oven, stovetop
Lake Sunapee Gathering Place, Serene Restored Barn
10.0 out of 10, Exceptional, (6)
"We are so happy we chose this home to stay at. The house is even better in person than photos. The description is accurate and the location truly offers something for everyone. Well stocked and clean! Check in/out was very easy and hosts are very welcoming and easy to contact. We would definitely stay again and recommend to family and friends!"
Lake Sunapee Gathering Place, Serene Restored Barn
Property grounds
Breathtaking Newbury Cottage w/ Deck on Chalk Pond
9.6 out of 10, Exceptional, (36)
"A cute cottage with a great view of the pond. Very clean and a nice layout. It had everything we needed. The pond was awesome and the community beach was very close with a great sandy swimming area."
Breathtaking Newbury Cottage w/ Deck on Chalk Pond
Oven, stovetop, dishwasher, coffee/tea maker
VT Cabin overlooking the West River and Village
10.0 out of 10, Exceptional, (19)
"The cabin was perfect for a getaway! Felt secluded however walkable to small village, and within 20 minutes to Stratton. Perfectly stocked to stay in for meals!"
The price is £274
includes taxes & fees
22 May - 23 May
VT Cabin overlooking the West River and Village
Combined shower/bathtub, hair dryer, towels, soap
SPACIOUS Custom 5 Bed Home 5min to Mount Sunapee! Garage, Hot Tub, Pool Table!
10.0 out of 10, Exceptional, (13)
"I booked a weekend stay on behalf of The Brotherhood: Men of Color Success Initiative at Salem State University. Samantha was a fantastic host from an organizing perspective. She was communicative, transparent, and answered my questions efficiently and effectively. She even refunded us for refilling the propane tank for the gas grill. Here is a review from The Brotherhood advisor, who stayed on the property with our students: "Sam—Thank you for sharing your beautiful Newbury, NH property with...
SPACIOUS Custom 5 Bed Home 5min to Mount Sunapee! Garage, Hot Tub, Pool Table!
Fridge, microwave, oven, stovetop
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
8.4 out of 10, Very good, (27)
"I was nervous reading about issues in other reviews, but we didn’t have a single problem. Both showers had plenty of hot water, access was a breeze, hot tub worked great and it was clean and comfortable. I had 9 people with us - teens and adults. The layout made it possible for us all to hang out as we wanted. Kitchen had a big pot for pasta and a griddle which made breakfasts easy. Great location made it easy for the kids to pop back for lunch. We had one little issue with the alarm when the...
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Exterior
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
9.8 out of 10, Exceptional, (107)
"Clean home close to downtown. Responsive owner. Highly recommended"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Exterior
Quaint lakefront home with a private deck, firepit, and dock
9.4 out of 10, Exceptional, (82)
"We had a great time staying at this cabin. It’s really well located and was perfect for our stay."
Quaint lakefront home with a private deck, firepit, and dock
Outdoor dining
Waterfront Cabin- look down on water from deck, private docks & fire pit
9.6 out of 10, Exceptional, (36)
"We enjoyed our time here!!! Beautiful view !"
Waterfront Cabin- look down on water from deck, private docks & fire pit
Indoor pool, a heated pool
Hike, Explore, Swim ~ Adventure in Vermont!
9.6 out of 10, Exceptional, (40)
"The owner had the place ready to go when we arrived. It was a late arrival, but there were outside lights that were warm and inviting. Plenty of space for our party of 12 (6 adults and 6 kids). Kitchen was welled stocked with cooking necessities, great hangout spaces in the basement and first floor, and a convenient space for ski boots and outer gear in the basement near parking. Kids absolutely loved the pool - and have the pruned hands to prove it. The location couldn't have been better, ~25...
Hike, Explore, Swim ~ Adventure in Vermont!
Don't see what you're looking for?
See all available properties in Charlestown
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.

Charlestown Holiday Rental Travel Info

Popular accommodation
Charlestown private holiday homes
Known landmarks
Maple Lanes, The Fort at No.4 Open Air Museum and Morningside Flight Park
International airport
Lebanon, NH (LEB-Lebanon Municipal)

Other types of properties in Charlestown you may be interested in

In-room safe, desk, blackout curtains, iron/ironing board
Days Inn by Wyndham Keene NH
2.0 star property
7.4 out of 10, Good, (874)
"Easy check in & friendly staff. But, neither card worked to unlock our door so had to go back to the front desk. TV remote worked but wouldn't change channel..had 1 channel with old westerns 😒"
The price is £80
includes taxes & fees
2 Jun - 3 Jun
Days Inn by Wyndham Keene NH
Interior entrance
Best Western Plus Keene Hotel
3.0 star property
8.2 out of 10, Very good, (1003)
"Nice pool, great breakfast "
The price is £119
includes taxes & fees
22 May - 23 May
Best Western Plus Keene Hotel
Hypo-allergenic bedding, in-room safe, desk, laptop workspace
Courtyard by Marriott Keene Downtown
3.0 star property
8.8 out of 10, Excellent, (903)
"The beds were comfy, the whole place was extremely clean and every employee we encountered was wonderful. I highly recommend a stay at this hotel, I know I’ll stay there again."
The price is £110
includes taxes & fees
19 May - 20 May
Courtyard by Marriott Keene Downtown
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.

Everything you need to know about Charlestown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Charlestown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Charlestown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Charlestown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Charlestown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Charlestown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Charlestown holiday rentals we have selected for you start as low as £149 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Charlestown rentals

At Expedia, we put the best Charlestown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Charlestown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Charlestown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Charlestown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Charlestown?

Yes, there are holiday rentals close to the most popular sights in Charlestown, or you can select a more secluded option if you're looking for a relaxing stay. Charlestown is known for its university setting and museums.

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

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: This holiday home rental outside of Charlestown is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

What’s there to see and do in Charlestown?

Cultural attractions include The Fort at No.4 Open Air Museum, whereas Connecticut River is a spot to enjoy nature. In the wider area, you’ll find Morningside Flight Park and Vermont Country Store.

What’s a holiday rental in Charlestown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Charlestown. Holiday rentals provide amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.

Recent reviews of Charlestown properties
Expedia verified reviews

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

4/5 Good
"Easy check in & friendly staff. But, neither card worked to unlock our door so had to go back to the front desk. TV remote worked but wouldn't change channel..had 1 channel with old westerns 😒"
A verified traveller stayed at Days Inn by Wyndham Keene NH
Posted 2 days ago
Days Inn by Wyndham Keene NH