Charlestown Vacation Rentals from AED 308: Search Short-Term Rentals

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

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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

Windsor

Brenda

AED 651 total

includes taxes & fees

17 Nov - 18 Nov

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

2. Cozy Village Condo-Okemo Shuttle

Ludlow

Mike T.

AED 917 total

includes taxes & fees

16 Nov - 17 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.

AED 1,485 total

includes taxes & fees

20 Nov - 21 Nov

A red house with a covered porch and a chimney.

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

Grafton

Neil S.

AED 1,366 total

includes taxes & fees

16 Nov - 17 Nov

A golf course with sand bunkers and a forested area.

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

Ludlow

AED 1,630 total

includes taxes & fees

20 Nov - 21 Nov

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

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

Clock Tower Base Area

tiliger01

AED 951 total

includes taxes & fees

18 Nov - 19 Nov

A view of a grassy area with a ski lift and a building in the background.

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

Clock Tower Base Area

Danna K.

AED 992 total

includes taxes & fees

18 Nov - 19 Nov

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

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

Ludlow

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

9. Adventure Cabin Hot Tub Sauna Trails Game Area

Cavendish

Katherine B.

AED 1,504 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Ludlow

Zach S.

AED 1,033 total

includes taxes & fees

19 Nov - 20 Nov

A golf course with a winding path, trees, and a hilly landscape.

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

Ludlow

Brian

AED 1,159 total

includes taxes & fees

19 Nov - 20 Nov

12. Charming Chester Farmhouse near Near VT Slopes

Chester Depot

Kimberly B.

AED 1,399 total

includes taxes & fees

22 Nov - 23 Nov

A golf course with a winding path, trees, and a distant mountain range.

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

Ludlow

Frank R.

AED 889 total

includes taxes & fees

18 Nov - 19 Nov

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

14. Explore the upper valley from this spacious Claremont Home

Claremont

Michael R.

AED 1,287 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Andover

Betsy S.

AED 1,497 total

includes taxes & fees

16 Nov - 17 Nov

A cozy cabin interior with a wooden ceiling, a round table with chairs, a fireplace, and a large window overlooking a snowy landscape.

16. Beautiful country cabin with hot tub and outdoor shower in Londonderry

Londonderry

Michael D.

AED 1,280 total

includes taxes & fees

16 Nov - 17 Nov

A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

17. Wellness Getaway with a Personal Sauna, and Private River Beach!

Newfane

Joseph P.

AED 1,041 total

includes taxes & fees

23 Nov - 24 Nov

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

18. Family Friendly Hilltop House In Putney Vermont

Putney

Wendy B.

AED 1,102 total

includes taxes & fees

16 Dec - 17 Dec

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

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

Cavendish

Mark G.

AED 2,123 total

includes taxes & fees

16 Nov - 17 Nov

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

20. Brook Road Cabin

Goshen

Elizabeth C.

AED 1,204 total

includes taxes & fees

16 Nov - 17 Nov

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Find vacation rentals that suit your style

Top Charlestown Hotel Reviews

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

JULIA

A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.

The Common Man Inn & Restaurant

Claremont

10/10 Excellent

Robert

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

Virginia

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

William

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

Four Columns Inn

Newfane

10/10 Excellent

Nettie

A bar area with a cake on a glass stand, plates, a pink napkin, and a rolled dessert on a plate.

Rosewood Country Inn

Bradford

10/10 Excellent

Anonymous traveler

A triangular wooden structure with a bench and a table, surrounded by lush greenery and a building in the background.

Otherland Hotel

Newfane

10/10 Excellent

The property is very well maintained and decorated. The room and bathroom are very clean. It has two very nice common area with 2 big windows that made them bright and sunny and cozy. It's also along a major highway so it's easy to find. The owners/operators of this hotel are very kind, thoughtful and accomodating to the needs of their guests. I especially and directly experienced their wonderful hospitality as a disabled person in a wheelchair. When I inquired about the accessibility of...

Rosalie

A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

Hampton Inn & Suites Keene

Keene

10/10 Excellent

kristin

A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

Pointe at Castle Hill Resort

Cavendish

10/10 Excellent

This is the second time we've stayed in a Suite room. King sized bed in the BR; kitchen with full-sized appliances, LR with pull-out Queen sofa, gas fireplace, bathroom with jetted tub! Very comfortable and fully equipped. Small things were so helpful - like doormats for dirty boots, a bench for putting on boots, a closet for skis, complementary packages of New England coffee, Aveda products in the bathroom, kitchen supplies like dish soap, dishwasher detergent, sponge, towels. Then larger...

Marion

A wooden table set with plates, cutlery, and a folded napkin.

The Carriage Barn Inn

Keene

10/10 Excellent

Richard

A well-maintained garden with a variety of plants and flowers, a wooden pergola, and a gravel path.

Fullerton Inn

Chester Depot

10/10 Excellent

Catherine

A stone fire pit with chairs around it, set in a grassy area with trees and a large building in the background.

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

10/10 Excellent

Jamie

A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

Keene Elm City Hotel, an Ascend Collection Hotel

Keene

10/10 Excellent

Kristine

A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

Main and Mountain Bar & Motel

Ludlow

10/10 Excellent

Anonymous traveler

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.

Charlestown Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Charlestown vacation rentals

1. Fat Sheep Farm & Cabins

2. Cozy Village Condo-Okemo Shuttle

3. Lakefront Family Fun Retreat

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

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

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

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

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

9. Adventure Cabin Hot Tub Sauna Trails Game Area

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

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

12. Charming Chester Farmhouse near Near VT Slopes

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

14. Explore the upper valley from this spacious Claremont Home

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

16. Beautiful country cabin with hot tub and outdoor shower in Londonderry

17. Wellness Getaway with a Personal Sauna, and Private River Beach!

18. Family Friendly Hilltop House In Putney Vermont

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

20. Brook Road Cabin

Find vacation rentals that suit your style

Top Charlestown Hotel Reviews

Best Western Springfield Hotel

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Charlestown?

What are some of the best vacation rentals that Charlestown has to offer?

How many vacation rentals are there in Charlestown?

What’s there to see and do in Charlestown?

What’s a vacation rental in Charlestown like?