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

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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 cottages

A wooden deck with a table and chairs overlooking a lake, surrounded by trees.

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

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is CA $212
CA $425 total
includes taxes & fees
Oct 4 - Oct 5
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A wooden deck with a table and chairs, surrounded by greenery and a wooden fence.

2. 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 CA $261
CA $425 total
includes taxes & fees
Nov 1 - Nov 2
Brook Road Cabin
A covered porch with a table and chairs, surrounded by a white railing, and hanging flower pots.

3. Hideaway Cottages, Cottage A

Hideaway Cottages, Cottage A
New London
9.6 out of 10, Exceptional, (71 reviews)
"Clean, comfy …… great night’s stay."
United States
Vicki and Bill M.
The price is CA $196
CA $308 total
includes taxes & fees
Oct 7 - Oct 8
Hideaway Cottages, Cottage A
A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

4. 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.
The price is CA $255
CA $753 total
includes taxes & fees
Nov 2 - Nov 3
Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
A single-story house with a green roof, surrounded by lush greenery and a well-maintained lawn.

5. Hideaway Cottages, Cottage B

Hideaway Cottages, Cottage B
New London
10.0 out of 10, Exceptional, (41 reviews)
"Character-filled old NH cabin nicely located on beautiful setting close to amenities"
United States
Brian
The price is CA $228
CA $351 total
includes taxes & fees
Oct 7 - Oct 8
Hideaway Cottages, Cottage B
A green wooden house with a sloped roof and a front porch.

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

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is CA $1,954
CA $3,059 total
includes taxes & fees
Oct 3 - Oct 4
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
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

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"My daughter and I were looking for someplace to meet in the middle… one coming from upstate New York and one coming from Massachusetts.This was not the first hotel we looked at. Fortunately it is the one we stayed at! The facility is very nice, even though older still very well maintained. Staff was exceptional! The location was perfect for just a fun getaway weekend. The downtown area has some lovely restaurants and shops but the restaurant at the resort was also very good. We enjoyed the area so much. We're talking about going again in the winter, even though neither of us have skied in ages!"
Michelle 3-night trip
Posted 6 hours ago
Jackson Gore Village, A Vail Resorts Property

Find out more about Charlestown

Charlestown Cottages information

Number of reviews
124
Accommodation
116 Cottages
Lowest Price
CA $308
Highest Price
CA $3,059

Frequently asked questions

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What is there to do in Charlestown near my cottage?
After you've settled into your hotel, set out and discover the amazing things Charlestown has to offer. The Fort at No.4 Open Air Museum is a popular attraction to add to your travel itinerary.

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