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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Charlestown vacation rentals

A modern living room with a sectional sofa, a wooden coffee table, and a large window with blinds.

1. 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
The price is P11,470
P18,682 total
includes taxes & fees
Sep 27 - Sep 28
Brook Road Cabin
A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

2. 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
The price is P13,410
P18,022 total
includes taxes & fees
Oct 22 - Oct 23
Fat Sheep Farm & Cabins
A spacious living area with a fireplace, a dining area, and a kitchen.

3. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is P85,841
P134,357 total
includes taxes & fees
Sep 27 - Sep 28
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
A cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

4. 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
The price is P11,495
P18,709 total
includes taxes & fees
Oct 19 - Oct 20
Brook Road Condo
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 Dalmatian behind the front desk"
April 2-night trip
Posted 2 hours ago
Pointe at Castle Hill Resort

Find out more about Charlestown

Search for holiday rentals in Charlestown on Expedia! You can easily find your home rentals, villas, holiday apartments in Charlestown using one of the methods below:

  • View our selection of featured holiday rentals in Charlestown
  • Use the map to find apartments and other holiday homes in the Charlestown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Charlestown while they last

Look no further and take a look at our great range of rental properties in Charlestown!

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.

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.