Holiday Rentals Charlestown from €159: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Charlestown holiday rentals

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

1. Fat Sheep Farm & Cabins

Windsor

Brenda

includes taxes & fees

17 Nov - 18 Nov

A red house with a covered porch and a chimney.

2. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

Kathy H.

includes taxes & fees

9 Nov - 10 Nov

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

3. Lakefront Family Fun Retreat

Newport

sean c.

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with stainless steel appliances, a wooden dining table set for four, and a seating area with a sofa and chairs.

4. Cozy Village Condo-Okemo Shuttle

Ludlow

Vanessa W.

includes taxes & fees

9 Nov - 10 Nov

A living room with a sofa, a bench, a fireplace, a TV, and a large window.

5. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Clock Tower Base Area

tiliger01

includes taxes & fees

11 Nov - 12 Nov

A building with multiple floors, a red curved structure, and a flower bed with purple flowers.

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

Clock Tower Base Area

Danna K.

includes taxes & fees

11 Nov - 12 Nov

A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

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

Ludlow

includes taxes & fees

11 Nov - 12 Nov

8. Charming Chester Farmhouse near Near VT Slopes

Chester Depot

Kimberly B.

includes taxes & fees

9 Nov - 10 Nov

A covered porch with wicker furniture, a table, and chairs.

9. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

Cavendish

Mark G.

includes taxes & fees

9 Nov - 10 Nov

A two-story house with a deck, surrounded by dense forest.

10. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

Chester

pauline

includes taxes & fees

9 Nov - 10 Nov

A staircase with wooden steps and white railings, leading to an upper floor.

11. Explore the upper valley from this spacious Claremont Home

Claremont

Michael R.

includes taxes & fees

9 Nov - 10 Nov

A wooden cabin interior with a staircase, a sofa, and a table.

12. Adventure Cabin Hot Tub Sauna Trails Game Area

Cavendish

Katherine B.

includes taxes & fees

11 Nov - 12 Nov

A room with a stone fireplace, wooden ceiling, and a window with curtains.

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

Ludlow

includes taxes & fees

9 Nov - 10 Nov

A two-story house with a porch, a staircase, and a front door.

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

Ludlow

Brian

includes taxes & fees

11 Nov - 12 Nov

A two-story house with a covered porch, a staircase, and a front door with a wreath.

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

Ludlow

Frank R.

includes taxes & fees

11 Nov - 12 Nov

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

Ludlow

Zach S.

includes taxes & fees

11 Nov - 12 Nov

A cozy living room with a large sectional sofa, a wooden coffee table, and a view of trees through a window.

17. Brook Road Cabin

Goshen

Elizabeth C.

includes taxes & fees

9 Nov - 10 Nov

A garden with a wooden pergola, purple flowers, and a river view.

18. Family Friendly Hilltop House In Putney Vermont

Putney

Susan G.

includes taxes & fees

9 Nov - 10 Nov

A cozy cabin interior with a wooden ceiling, a sofa, a red armchair, a small table with magazines, and a window with curtains.

19. Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you!

Andover

Betsy S.

includes taxes & fees

21 Nov - 22 Nov

A red brick building with a classical facade, a covered walkway, and a well-maintained lawn.

20. Brook Road Condo

Goshen

Margaret

includes taxes & fees

9 Nov - 10 Nov

View all properties

Find holiday rentals that suit your style

Top Charlestown Hotel Reviews

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

Harvest Barn Inn

Bellows Falls

10/10 Excellent

philip

A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

Best Western Springfield Hotel

Springfield

10/10 Excellent

Ruggiero

A large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.

The Inn at Weathersfield

Perkinsville

8/10 Good

Anonymous traveller

A multi-story building with a central staircase, outdoor seating, and a sunset sky.

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

10/10 Excellent

We were there at the end of May. We particularly liked the view of the mountain from our window. The hotel is split over several attractive buildings, all sited on what used to be a ski resort. We were told that it was a "time share" which means that there is no daily maid service, which made no difference to us at all. The accommodation was excellent, so much so that we extended our stay. The staff were very welcoming. The large indoor pool was also very impressive. There is also an outdoor...

Anonymous traveller

Fat Sheep Farm & Cabins

Windsor

10/10 Excellent

This was a wonderful one night stay as part of our leaf peeping trip to Vermont from the UK. One thing to be aware of is that GPS/satnav is really bad in this area. Make sure you take printed written instructions of how to find them. The cabin is absolutely lovely. It’s really well equipped, especially the kitchen which has good quality knives, saucepans, frying pans, etc important if you’re going to be doing your own cooking. Lovely little touches of leaving a couple of home-made scones and...

David

A stone-clad building entrance with a covered patio and benches.

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Newbury

10/10 Excellent

Rachel

A bay window seating area with a round table, a potted plant, and a garland with pine cones and lights.

The Hartness House

Springfield

10/10 Excellent

Christine

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

Stone Hearth Inn and Eatery

Chester

10/10 Excellent

Timothy

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

Four Columns Inn

Newfane

8/10 Good

We only had an opportunity to stay one night stay but overall had a very pleasant experience. The room was really nice apart from the wierd location of the television . The bar was "like a real bar " and the lady serving was great ( as was the live entertainment ). Our dining experience has room for improvement although the staff were really nice . Breakfast was "OK" . Good coffee . The owner was extremely friendly and the location and grounds are beautiful . Check in was a little fluffy - I...

Philip

A historic brick building with a porch and a sign reading "Burrell House."

The Burrell House

Keene

10/10 Excellent

Lauren

A dining area with wooden tables and chairs, large windows with a view of trees, and a bench along the wall.

The Carriage Barn Inn

Keene

10/10 Excellent

tricia

Frequently Asked Questions

Can I find a holiday rental in Charlestown?

Yes, there are holiday rentals close to the most popular sights in Charlestown, or you can select a more secluded option if you're looking for a relaxing stay. Charlestown is known for its university setting and museums.

How many holiday rentals are there in Charlestown?

With 3 Expedia holiday rentals, you're guaranteed 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 holiday rental in Charlestown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Charlestown. Holiday rentals provide amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.

Search Holiday Rentals in Charlestown

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Charlestown holiday rentals

1. Fat Sheep Farm & Cabins

2. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

3. Lakefront Family Fun Retreat

4. Cozy Village Condo-Okemo Shuttle

5. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

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

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

8. Charming Chester Farmhouse near Near VT Slopes

9. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

10. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

11. Explore the upper valley from this spacious Claremont Home

12. Adventure Cabin Hot Tub Sauna Trails Game Area

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

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

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

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

17. Brook Road Cabin

18. Family Friendly Hilltop House In Putney Vermont

19. Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you!

20. Brook Road Condo

Find holiday rentals that suit your style

Top Charlestown Hotel Reviews

Harvest Barn Inn

10/10 Excellent

Frequently Asked Questions

Can I find a holiday rental in Charlestown?

How many holiday rentals are there in Charlestown?

What’s there to see and do in Charlestown?

What’s a holiday rental in Charlestown like?