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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Charlestown vacation rentals

A red house with a covered porch and a chimney.

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, (172 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
Oct 12 - Oct 13
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

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.
$378 nightly
The price is $410
Nov 3 - Nov 4
Total with taxes and fees
Lakefront Family Fun Retreat
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

3. 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
$208 nightly
The price is $235
Nov 2 - Nov 3
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A view of a grassy area with a ski lift and a building in the background.

4. 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)
"Property is on 4th floor almost at the end, so you have to walk the most with heavy bags..that was pain.. had problems with heating and cooling system. Also requested for 1 hour late check out at the time of booking, never received any response on top cleaning stuffs were sent to the property sharp at 10 am. Our friends rented another property on the same building and they could easily checked out late at 12:00 pm. Otherwise we enjoyed our stay and proximity to the slope is unparallel."
United States
Indrajit A.
$236 nightly
The price is $266
Oct 12 - Oct 13
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
$262 nightly
The price is $296
Oct 26 - Oct 27
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Dining

6. 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.
$377 nightly
The price is $422
Oct 20 - Oct 21
Total with taxes and fees
Charming Chester Farmhouse near Near VT Slopes
A two-story house with a porch, a staircase, and a front door.

7. 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
$240 nightly
The price is $271
Oct 5 - Oct 6
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
A two-story house with a porch, a staircase, and a front door.

8. 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.
$211 nightly
The price is $239
Oct 5 - Oct 6
Total with taxes and fees
Cozy Studio Condo with Great Location, WiFi & Kitchenette
A golf course with a winding path, trees, and a distant mountain range.

9. Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (34 reviews)
"the home was clean and very nice. "
United States
Frank R.
$205 nightly
The price is $232
Oct 5 - Oct 6
Total with taxes and fees
Efficient condo near slopes with kitchenette & great location
A patio area with outdoor furniture, a small garden with purple flowers, and a white building in the background.

10. 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.
$536 nightly
The price is $582
Oct 8 - Oct 9
Total with taxes and fees
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
A garden with a wooden pergola, purple flowers, and a river view.

11. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (64 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
$235 nightly
The price is $263
Oct 20 - Oct 21
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
A room with a bunk bed, a dresser, a lamp, and a window with a view of greenery.

12. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
$412 nightly
The price is $454
Oct 5 - Oct 6
Total with taxes and fees
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A covered porch with wicker furniture, a table, and chairs.

13. Renovated Vermont Retreat with mountain views near Okemo & Killington for 8

Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
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.
$484 nightly
The price is $542
Nov 2 - Nov 3
Total with taxes and fees
Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
A cozy cabin interior with a TV displaying 'NETFLIX', a fireplace, wooden walls, a window with a forest view, and a comfortable seating area.

14. Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Cavendish
10.0 out of 10, Exceptional, (28 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
$420 nightly
The price is $454
Oct 28 - Oct 29
Total with taxes and fees
Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
A picnic table and a fire pit by a lake with a forest in the background.

15. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
$271 nightly
The price is $298
Oct 4 - Oct 5
Total with taxes and fees
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

16. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
$198 nightly
The price is $215
Nov 1 - Nov 2
Total with taxes and fees
Fat Sheep Farm & Cabins
A wooden cabin with a balcony, surrounded by trees.

17. 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
9.6 out of 10, Exceptional, (27 reviews)
"Amazing weekend stay with our pup! Looking forward to staying here in the summer! "
United States
Naydene G.
$395 nightly
The price is $429
Oct 4 - Oct 5
Total with taxes and fees
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
A picnic table and a fire pit by a lake with a forest in the background.

18. 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)
"Great location and very cozy cottage. Well-appointed place to stay and accurately described in its listing. "
United States
jeremy a.
$279 nightly
The price is $315
Oct 4 - Oct 5
Total with taxes and fees
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A cozy living room with a large sectional sofa, a wooden coffee table, and a view of trees through a window.

19. Brook Road Cabin

Brook Road Cabin
Goshen
9.6 out of 10, Exceptional, (18 reviews)
"Would go back!"
United States
Elizabeth C.
$296 nightly
The price is $321
Oct 5 - Oct 6
Total with taxes and fees
Brook Road Cabin
A spacious living area with hardwood flooring, a staircase, a black entertainment unit, a door, and a window with blinds.

20. Explore the upper valley from this spacious Claremont Home

Explore the upper valley from this spacious Claremont Home
Claremont
$339 nightly
The price is $368
Oct 4 - Oct 5
Total with taxes and fees
Explore the upper valley from this spacious Claremont Home
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 Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

8/10 Good
"Overall, I really liked this hotel. It was very clean and well maintained. My one feedback would be to repair the beds. Because the beds were making a lot of noise and we had problem sleeping as little movements were making a lot of sound. Also there is not complimentary breakfast... Other than these this hotel is highly recommended... my personal rating is 7/10 😃😃"
Bishajit 1-night trip
Posted 8 hours ago
The Upper Pass Lodge at Magic Mountain

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 $215 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.

How many vacation rentals are there in Charlestown?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Charlestown stay.

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.