A grassy field with a wooden fence, surrounded by autumn-colored trees and a hill in the background.

Charlestown Vacation Rentals

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Charlestown vacation rentals

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

1. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (14 reviews)
"This property was extremely beautiful and peaceful. Loved being able to walk around the farm and say hi to the animals. The views of the mountains from the cabin or gorgeous, we enjoyed having our coffee on the porch each morning. Having fresh eggs and scones in our cabin upon arrival was a very nice surprise. Will definitely be staying there again."
United States
Brenda
$164 nightly
The price is $179
Nov 11 - Nov 12
Total with taxes and fees
Fat Sheep Farm & Cabins
A red house with a covered porch and a chimney.

2. 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, (174 reviews)
"We had such a great time! Those is a well taken care of, clean, cozy property. We would absolutely visit again!!"
United States
Kathy H.
$327 nightly
The price is $366
Oct 28 - Oct 29
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.

3. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Had a lot here to use and The place was very cute. It’s good if you have small kids they have a lot for that sort of thing. Very clean as well"
United States
sean c.
$378 nightly
The price is $410
Nov 1 - Nov 2
Total with taxes and fees
Lakefront Family Fun Retreat
A wooden cabin interior with a staircase, a sofa, and a table.

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

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Cavendish
10.0 out of 10, Exceptional, (29 reviews)
"A very clean and modern cabin. Loved the amenities like the paddle boards, kayaks and hot tub.!"
United States
Katherine B.
$377 nightly
The price is $406
Nov 11 - Nov 12
Total with taxes and fees
Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
A staircase with wooden steps and white railings, leading to an upper floor.

5. Explore the upper valley from this spacious Claremont Home

Explore the upper valley from this spacious Claremont Home
Claremont
10.0 out of 10, Exceptional, (1 review)
"Nice place."
United States
Michael R.
$339 nightly
The price is $368
Oct 28 - Oct 29
Total with taxes and fees
Explore the upper valley from this spacious Claremont Home
A cozy living room with a large sectional sofa, a wooden coffee table, and a view of trees through a window.

6. Brook Road Cabin

Brook Road Cabin
Goshen
9.6 out of 10, Exceptional, (18 reviews)
"Would go back!"
United States
Elizabeth C.
$286 nightly
The price is $310
Oct 28 - Oct 29
Total with taxes and fees
Brook Road Cabin
A cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

7. Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
8.8 out of 10, Excellent, (3 reviews)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
$252 nightly
The price is $274
Nov 26 - Nov 27
Total with taxes and fees
Brook Road Condo
A covered porch with wicker furniture, a table, and chairs.

8. 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, (3 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
$463 nightly
The price is $519
Nov 4 - Nov 5
Total with taxes and fees
Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
A golf course with a winding path, trees, and a hilly landscape.

9. First-floor downtown studio near dining and gear shops, under a mile to Okemo

First-floor downtown studio near dining and gear shops, under a mile to Okemo
Ludlow
8.8 out of 10, Excellent, (14 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
Oct 28 - Oct 29
Total with taxes and fees
First-floor downtown studio near dining and gear shops, under a mile to Okemo
A golf course with sand bunkers and a forested area.

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
$398 nightly
The price is $438
Oct 28 - Oct 29
Total with taxes and fees
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A two-story house with a porch, a staircase, and a front door.

11. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

Downtown Ludlow condo with electric fireplace, shuttle stop across the street
Ludlow
8.8 out of 10, Excellent, (27 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
$240 nightly
The price is $271
Oct 28 - Oct 29
Total with taxes and fees
Downtown Ludlow condo with electric fireplace, shuttle stop across the street
A golf course with a winding path, trees, and a distant mountain range.

12. Compact downtown studio condo with kitchenette near the Okemo slopes

Compact downtown studio condo with kitchenette near the Okemo slopes
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 28 - Oct 29
Total with taxes and fees
Compact downtown studio condo with kitchenette near the Okemo slopes
A yellow building with a porch and a sign that reads "Brook Road Inn."

13. Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (15 reviews)
"Nice place for a mountain stay"
United States
Meghan B.
$296 nightly
The price is $321
Oct 28 - Oct 29
Total with taxes and fees
Brook Road Condo
A view of a grassy area with a ski lift and a building in the background.

14. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
$236 nightly
The price is $266
Oct 28 - Oct 29
Total with taxes and fees
Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

15. Condo a short walk to the Sachem trail with seasonal pool and tennis

Condo a short walk to the Sachem trail with seasonal pool and tennis
Ludlow
$262 nightly
The price is $296
Oct 28 - Oct 29
Total with taxes and fees
Condo a short walk to the Sachem trail with seasonal pool and tennis
A picnic table and a fire pit by a lake with a forest in the background.

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

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
$308 nightly
The price is $339
Oct 28 - Oct 29
Total with taxes and fees
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A modern living room with a sectional sofa, a wooden coffee table, and a large window with blinds.

17. 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
Oct 28 - Oct 29
Total with taxes and fees
Brook Road Cabin
A view through a window with a wooden frame, revealing a forested area with snow on the ground.

18. Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
$243 nightly
The price is $274
Oct 28 - Oct 29
Total with taxes and fees
Cozy cabin in charming Londonderry
Dining

19. 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
Nov 5 - Nov 6
Total with taxes and fees
Charming Chester Farmhouse near Near VT Slopes
A multi-story building with a central staircase, outdoor picnic tables, and a clear sky.

20. 2BR Duplex Villa w/ Balcony | Game Room + Fire Pit

2BR Duplex Villa w/ Balcony | Game Room + Fire Pit
Brownsville
$258 nightly
The price is $281
Nov 1 - Nov 2
Total with taxes and fees
2BR Duplex Villa w/ Balcony | Game Room + Fire Pit
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
"The indoor pool was super clean, hot tub clean. Property is in great shape Will go back if have a chance."
Cheryl 2-night trip
Posted 3 hours ago
Pointe at Castle Hill Resort

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 $179 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.