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Charlestown Vacation Rentals

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Vacation Rentals in Charlestown

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, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
$230 nightly
The price is $260
Nov 23 - Nov 24
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
3 bedrooms, internet, bed sheets
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Andover
9.0 out of 10, Wonderful, (29)
"Really enjoyed the place for a quiet weekend together."
United States
Eric B.
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Fridge, microwave, oven, stovetop
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ludlow
8.0 out of 10, Very Good, (41)
"Plenty of space and the two living rooms are great because the upstairs living room is very small."
United States
Brad H.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
TV
Hideaway Cottages, Cottage B

Hideaway Cottages, Cottage B

New London
10.0 out of 10, Exceptional, (24)
"Cozy cabin, easy check in, Wifi available."
United States
Marian R.
$154 nightly
The price is $167
Nov 24 - Nov 25
Total with taxes and fees
Hideaway Cottages, Cottage B
Property grounds
Owl's Nest Treehouse

Owl's Nest Treehouse

Alstead
10.0 out of 10, Exceptional, (11)
"Great place . Would highly recommend it.!"
United States
Peter G.
$309 nightly
The price is $335
Nov 30 - Dec 1
Total with taxes and fees
Owl's Nest Treehouse
Terrace/patio
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Townshend
10.0 out of 10, Exceptional, (6)
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
Exterior
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Ludlow
9.8 out of 10, Exceptional, (127)
"Beautiful place! Enjoyed our stay!"
United States
Cathy B.
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
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, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
$330 nightly
The price is $370
Nov 19 - Nov 20
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior detail
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Ludlow
10.0 out of 10, Exceptional, (95)
"We had a lovely time. The cabin is cozy and quiet and being on the lake was wonderful. "
United States
Leah C.
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore
Exterior
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

Ludlow
9.8 out of 10, Exceptional, (40)
"Had a great and comfortable stay with family. House is clean and had all the amenities and supplies needed. "
United States
Aruna G.
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
Interior
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Londonderry
8.6 out of 10, Excellent, (8)
"We had a wonderful stay."
United States
Joshua
$502 nightly
The price is $567
Nov 24 - Nov 25
Total with taxes and fees
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Property grounds
Idyllic Lakefront House Suited Two Families

Idyllic Lakefront House Suited Two Families

Ludlow
9.6 out of 10, Exceptional, (171)
"House and grounds were well maintained. "
United States
Dorothy Y.
Idyllic Lakefront House Suited Two Families
Property grounds
Winterplace at Okemo

Winterplace at Okemo

4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (25)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
United States
Kathia
Winterplace at Okemo
Fridge, microwave, oven, stovetop
Hideaway Cottages, Cottage A

Hideaway Cottages, Cottage A

New London
9.6 out of 10, Exceptional, (45)
"Really clean, comfortable country cottage. Pleased with our stay. 😁"
United States
Jonathan
$134 nightly
The price is $145
Nov 30 - Dec 1
Total with taxes and fees
Hideaway Cottages, Cottage A
Solitude Village Two Bedroom Suite Mountainside | Private kitchen | Fridge, microwave, stovetop, toaster
Solitude Village at Okemo

Solitude Village at Okemo

4.0 star property
Clock Tower Base Area
8.0 out of 10, Very Good, (31)
"Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also."
United States
Larry
Solitude Village at Okemo
Interior
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

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

2.0 star property
Cavendish
10.0 out of 10, Exceptional, (9)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$284 nightly
The price is $309
Nov 20 - Nov 21
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Exterior
Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo

Woodstock
9.8 out of 10, Exceptional, (13)
"Unique settings. Loved the accommodations "
United States
Gabriela
$171 nightly
The price is $187
Nov 19 - Nov 20
Total with taxes and fees
Treehouse at Wise Pines- NoBo
Exterior
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Ludlow
9.8 out of 10, Exceptional, (179)
"Great stay, for a golf trip with 12 guys, there was plenty of room for everyone, would definitely recommend and will be trying to come back and stay as well!"
United States
Matt C.
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Exterior
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Ludlow
9.6 out of 10, Exceptional, (19)
"The house, its location, and dock are real nice. Would come here again."
United States
Wendy G.
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Property grounds
Treehouse at Wise Pines- SoBo

Treehouse at Wise Pines- SoBo

Woodstock
9.8 out of 10, Exceptional, (24)
"What a unique experience staying in a literal tree house. The bathroom shared with the other tree house was so wonderfully built as is the barn that it resides in. I only stayed one night and wished I stayed multiple nights. I will definitely consider staying here again for future MTB trips in the area! "
United States
Taku S.
$171 nightly
The price is $187
Nov 19 - Nov 20
Total with taxes and fees
Treehouse at Wise Pines- SoBo
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

The Putney Inn

The Putney Inn

10/10 Excellent
"Nice rooms and quite "
Justin 3-night trip
Posted 5 days ago
The Putney Inn

Find out more about Charlestown

Everything you need to know about Charlestown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Charlestown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Charlestown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Charlestown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $145 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Charlestown rentals

At Expedia, we put the best Charlestown vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: 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 3 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 selection of games.

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 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.