Charlemont Holiday Houses

A wooden covered bridge with a 'DANGER KEEP OFF DAM' sign, surrounded by lush greenery.

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Our top choices for Charlemont holiday homes

A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

1. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

includes taxes & fees

30 Sept - 1 Oct

A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

2. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

includes taxes & fees

26 Oct - 27 Oct

A hallway with wooden flooring, white walls, and a bed in the background.

3. Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls

maureen

includes taxes & fees

6 Oct - 7 Oct

A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

4. Lovely 2nd Floor Apartment

Greenfield

Christa B.

includes taxes & fees

22 Oct - 23 Oct

A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

5. Spacious 5BR w/ Hot Tub & Games

Colrain

Staci M.

includes taxes & fees

4 Oct - 5 Oct

An aerial view of a house surrounded by a forest with autumn foliage.

6. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Whitingham

Jonathan

includes taxes & fees

30 Sept - 1 Oct

A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

7. The Greylock Cabin

Florida

Margaret M.

includes taxes & fees

5 Oct - 6 Oct

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

8. Cozy Home in Pownal VT

Pownal

Jess M.

includes taxes & fees

8 Oct - 9 Oct

A two-story house with a porch, surrounded by trees and snow.

9. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Bennington

Malika R.

includes taxes & fees

30 Sept - 1 Oct

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

10. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Nancy M.

includes taxes & fees

5 Oct - 6 Oct

A kitchen with white cabinets, a wooden dining table, and pendant lights.

11. A roomy remodeled retreat close to MassMoCA

North Adams

Jennifer O.

includes taxes & fees

13 Oct - 14 Oct

A two-story white house with a red door, surrounded by autumn foliage and a stone wall.

12. The Eagles Wing at The CHM - Private Apartment

Dover

Matthew C.

includes taxes & fees

30 Sept - 1 Oct

A bedroom with a bed, bedside tables, a window, and a radiator.

13. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

Woodford

includes taxes & fees

30 Sept - 1 Oct

A cozy interior with a wooden ceiling, a large window, and a table with chairs.

14. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

Wilmington

Natalie

includes taxes & fees

6 Oct - 7 Oct

A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

15. Walk To Town, Hottub, Firepit, Games, Mt Snow

Wilmington

Jeremy P.

includes taxes & fees

30 Sept - 1 Oct

A red house with a porch, surrounded by a grassy yard and trees.

16. Two Brooks Lodge

Bennington

"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...

Hunter

includes taxes & fees

30 Sept - 1 Oct

A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

17. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Williamstown

Michelle B.

includes taxes & fees

30 Sept - 1 Oct

A dining area with a long table and chairs, large windows with a view of trees, and a barbecue grill outside.

18. MtSnow* HotTub* Pool * AirHockeyPingPong Darts

Wilmington

includes taxes & fees

30 Sept - 1 Oct

A room with white paneled walls, a wooden bench, a teal cushion, a vase with flowers, a framed picture, and a shelf with books and a small electronic device.

19. Cozy Vermont Tiny Home Get Away

Brattleboro

includes taxes & fees

30 Oct - 31 Oct

A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

20. Modern Mount Snow Gnarvana - Steps to Carinthia

Dover

Lynn B.

includes taxes & fees

30 Sept - 1 Oct

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Top Charlemont Hotel Reviews

The Williams Inn

10/10 Excellent

"Amazing"

Latchis Hotel

10/10 Excellent

"This place is a gem. I love and like the proximity to the train station, Brattleboro Food Coop, River Art School and Brattleboro Museum and Art Center, I visited twice: first with my teen son and husband, and the second by myself, and both times were great. There are signs of the passing of time in this lovely Art Deco structure, and that adds to its beauty, Super courteous staff The first time we watched a movie, so if you stay at the hotel, please treat yourself to that or some of their baskets. I missed eating at their restaurant, so I guess next time. My husband loved that there was always coffee for him, and my son loved our mini fridge and microwave. We love the history of this place and how is part of the larger arts and culture scene of Brattleboro"

Berkshire Mountain Lodge

8/10 Good

"The problem with the suites is that the cooking smell of the adjoining kitchen can really permeate throughout the entire space. So whoever cooked like a tomato sauce or something before I was there, I could really smell it in the bedroom. The bed was very comfortable though. The room was clean. The bathroom could use some updating. The staff were very nice."

Grand Summit Resort, A Vail Resorts Property

8/10 Good

"What I like is the room was well stocked, very clean and the staff is very helpful. What I did not like is the parking is very inconvenient and is quite a walk which is never fun in bad weather. They need more luggage carts. It looked like they have about 5 or 6 for about a 200 room hotel. There was only one place on the property to get breakfast in the morning. There is a stove and refrigerator in the room. I had no idea before hand those would be available!"

River Valley Inn

10/10 Excellent

"Chris helped me out tremendously. After flying all the way from Tennessee, I was exhausted and didn’t know what I was going to do. Chris went above and beyond to help me get a room, even though it was already very late. I truly appreciate your kindness and willingness to help me when I needed it most. ❤️🙏"

Find out more about Charlemont

Charlemont Holiday Homes information

Number of reviews	375
Accommodation	449 Holiday Homes
Lowest Price	NZ$358
Highest Price	NZ$1,335

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Charlemont holiday homes

1. 5BR Berkshire Home Mins To The Mountain

2. Private bed with En-suite bathroom Marigold Room