Holiday Homes in Charlestown

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Find holiday rentals that suit your style

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Charlestown holiday homes

A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

1. 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.
The price is AU$579
includes taxes & fees
13 Nov - 14 Nov
Lakefront Family Fun Retreat
A cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

2. 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 AU$436
includes taxes & fees
26 Nov - 27 Nov
Brook Road Condo
A two-story house with a deck, surrounded by dense forest.

3. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is AU$1,365
includes taxes & fees
14 Nov - 15 Nov
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A golf course with sand bunkers and a forested area.

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is AU$625
includes taxes & fees
13 Nov - 14 Nov
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Dining

5. 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.
The price is AU$542
includes taxes & fees
6 Dec - 7 Dec
Charming Chester Farmhouse near Near VT Slopes
A yellow building with a porch and a sign that reads "Brook Road Inn."

6. 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.
The price is AU$475
includes taxes & fees
22 Nov - 23 Nov
Brook Road Condo
A garden with a wooden pergola, purple flowers, and a river view.

7. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (66 reviews)
"Had a perfect, relaxing stay in this gorgeous spot. Everything was terrific. Highly recommend!"
United States
Wendy B.
The price is AU$410
includes taxes & fees
17 Nov - 18 Nov
Family Friendly Hilltop House In Putney Vermont
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

8. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (114 reviews)
"Wendi was very responsive when I had questions. We enjoyed our weekend getaway. Great location we walked into town to the Farmers Market Sunday."
United States
Tina l.
The price is AU$721
includes taxes & fees
2 Dec - 3 Dec
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
A cozy living room with a stone fireplace, large windows, and a wooden ceiling.

9. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is AU$940
includes taxes & fees
22 Nov - 23 Nov
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a hanging light fixture.

10. Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee

Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
Sunapee
10.0 out of 10, Exceptional, (59 reviews)
"Wonderful place to stay for our trip. Great location and the house was nicely updated. "
United States
Andrew W.
The price is AU$672
includes taxes & fees
15 Nov - 16 Nov
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

11. SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!

SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!
Newbury
9.8 out of 10, Exceptional, (21 reviews)
"Neat place, close to two ski mountains. "
United States
COLLEEN K.
The price is AU$1,516
includes taxes & fees
18 Nov - 19 Nov
SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!
A spacious living room with a high ceiling, wooden beams, a fireplace, and large windows.

12. Game Room, Fire Pit & Views! Spacious Ludlow Home

Game Room, Fire Pit & Views! Spacious Ludlow Home
Ludlow
The price is AU$1,101
includes taxes & fees
15 Nov - 16 Nov
Game Room, Fire Pit & Views! Spacious Ludlow Home
A wooden cabin with multiple windows and a balcony, surrounded by trees.

13. Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee

Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
Newbury
10.0 out of 10, Exceptional, (32 reviews)
"Great experience and an amazing property"
United States
Tim D.
The price is AU$732
includes taxes & fees
15 Nov - 16 Nov
Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
A spacious living room with a fireplace, large windows, and a cozy seating area.

14. @SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Sunapee
10.0 out of 10, Exceptional, (28 reviews)
"The perfect winter stay for our family! Perfect location, close to Mount Sunapee. Gorgeous views and home. Host was extremely welcoming and responsive, and the whole stay was easy."
United States
Amanda R.
The price is AU$873
includes taxes & fees
18 Nov - 19 Nov
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

15. Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (6 reviews)
"Everything was perfect for our weekend stay. Host responded immediately to our questions. House had all the amenities for an enjoyable time!"
United States
Mary P.
The price is AU$884
includes taxes & fees
13 Nov - 14 Nov
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

16. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
9.8 out of 10, Exceptional, (6 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is AU$659
includes taxes & fees
23 Nov - 24 Nov
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

17. New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (24 reviews)
"Super friendly host, great property and very clean home close to town."
United States
Larissa R.
The price is AU$815
includes taxes & fees
14 Nov - 15 Nov
New Ludlow Village Home with Stunning Okemo Mountain View
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

18. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (28 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is AU$515
includes taxes & fees
17 Nov - 18 Nov
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A spacious living room with a large sectional sofa, a glass coffee table, and a high ceiling with exposed wooden beams.

19. "Big Sky" Retreat Atop Sunapee / Ski + Lake Life

"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
Newbury
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house in a nice location. Close to the lake, ski area and hiking. It was the perfect space to have a mini reunion with some friends."
United States
William B.
The price is AU$1,501
includes taxes & fees
16 Nov - 17 Nov
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
A spacious living room with a high ceiling, exposed wooden beams, and a large window providing natural light.

20. "Big Sky" Retreat Atop Sunapee with Overflow Unit

"Big Sky" Retreat Atop Sunapee with Overflow Unit
Newbury
10.0 out of 10, Exceptional, (1 review)
The price is AU$1,888
includes taxes & fees
16 Nov - 17 Nov
"Big Sky" Retreat Atop Sunapee with Overflow Unit
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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Learn more about Charlestown

This historic New England village invites you to explore the Fort at No. 4, where costumed interpreters bring colonial life to vibrant reality. Wander Main Street's well-preserved 18th-century buildings before asking locals about nearby hiking trails in the Connecticut River Valley.

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

Top reviews in Charlestown

Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
Keene

10/10 Excellent

Great location, bedroom and bathroom very nice and good breakfast
Australia
David
Reviewed August 22, 2023
Fairfield Inn & Suites by Marriott Keene Downtown

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