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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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Charlestown vacation rentals

Exterior

1. 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, (170 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.
$331 nightly
The price is $371
Aug 25 - Aug 26
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Property grounds

2. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
$405 nightly
The price is $439
Sep 1 - Sep 2
Total with taxes and fees
Lakefront Family Fun Retreat
Property grounds

3. 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)
"Lots of steps but great space. Blankets were dirty, which was the only downside. "
United States
serena m.
$236 nightly
The price is $266
Aug 25 - Aug 26
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Dining

4. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
$380 nightly
The price is $426
Aug 25 - Aug 26
Total with taxes and fees
Charming Chester Farmhouse near Near VT Slopes
Interior

5. Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (51 reviews)
"We had a fantastic stay! Can’t wait to return for a summer or fall trip. Cabin was wonderful, clean and full of amenities. It is a plus having access to laundry services."
United States
John H.
$330 nightly
The price is $353
Aug 25 - Aug 26
Total with taxes and fees
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Living area

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
$256 nightly
The price is $289
Aug 25 - Aug 26
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Exterior

7. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
9.8 out of 10, Exceptional, (16 reviews)
"Great stay, house is clean and has everything you’de ever need. Perfect location to explore the ludlow area. Thanks Bob, we enjoyed ourselves "
United States
Tyler
$229 nightly
The price is $259
Aug 25 - Aug 26
Total with taxes and fees
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Living area

8. 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.
$204 nightly
The price is $231
Aug 31 - Sep 1
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Exterior

9. Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Ludlow
9.0 out of 10, Wonderful, (14 reviews)
"Great place!"
United States
Darcie L.
$279 nightly
The price is $315
Aug 25 - Aug 26
Total with taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Interior

10. 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.
$543 nightly
The price is $608
Aug 26 - Aug 27
Total with taxes and fees
Terrific 3-bedroom cottage with AC in charming Cavendish
Property grounds

11. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
$268 nightly
The price is $301
Sep 1 - Sep 2
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
Golf

12. 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
$273 nightly
The price is $309
Aug 25 - Aug 26
Total with taxes and fees
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Golf

13. 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.
$205 nightly
The price is $232
Aug 25 - Aug 26
Total with taxes and fees
Efficient condo near slopes with kitchenette & great location
Living area

14. Brook Road Cabin

Brook Road Cabin
Goshen
9.6 out of 10, Exceptional, (18 reviews)
"Would go back!"
United States
Elizabeth C.
$300 nightly
The price is $326
Aug 25 - Aug 26
Total with taxes and fees
Brook Road Cabin
Living area

15. 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.
$381 nightly
The price is $430
Sep 7 - Sep 8
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Family Cabin, 2 Bedrooms, Mountain View | Living room

16. Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.4 out of 10, Good, (10 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
$282 nightly
The price is $306
Aug 25 - Aug 26
Total with taxes and fees
Brook Road Cabin
Living area

17. Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
$446 nightly
The price is $499
Sep 13 - Sep 14
Total with taxes and fees
Cozy Private Cabin in Andover - Fireplace & Hot tub
Interior

18. 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, (27 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
$330 nightly
The price is $353
Aug 25 - Aug 26
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Outdoor dining

19. Hideaway Cottages, Cottage A

Hideaway Cottages, Cottage A
New London
9.6 out of 10, Exceptional, (71 reviews)
"Awesome placeThe host was attentive to every needWould highly recommend"
United States
paul K.
$200 nightly
The price is $217
Aug 31 - Sep 1
Total with taxes and fees
Hideaway Cottages, Cottage A
Terrace/patio

20. Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (52 reviews)
"We had a very lovely stay. "
United States
mary c.
$640 nightly
The price is $694
Sep 3 - Sep 4
Total with taxes and fees
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
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

8/10 Good
"I would recommend the Putney inn"
Donna 1-night trip
Posted 6 hours 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 $217 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?

Family Friendly Hilltop House In Putney Vermont: This vacation home rental near Charlestown is located on a lake and has a balcony, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Charlestown?

Connecticut River State Park and Connecticut River 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.