Charlemont Holiday Rentals, Massachusetts: Private House Rentals

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

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Go beyond your typical stay in Charlemont

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Hot tub

Family friendly

Cottage

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Our top choices for Charlemont hotels

Hotel

Reserve now, pay later

Pet-friendly

Breakfast included

Resort

1. Doveberry Inn

West Dover

฿4,996

฿5,496 total

includes taxes & fees

22 Aug - 23 Aug

A two-story house with a red door, green shutters, and a snow-covered front yard.

A golf course with a brick pathway, wooden boxes, and a tee box.

A window with a view of a grassy field and a bench.

A red building with white trim, surrounded by lush greenery and fruit trees.

2. Centennial House

Northfield

Amy

฿5,930

฿6,268 total

includes taxes & fees

31 Aug - 1 Sept

3. Shelburne Springs Hotel

Shelburne

฿12,386

฿13,835 total

includes taxes & fees

17 Sept - 18 Sept

An indoor swimming pool with clear water, surrounded by windows with a view of trees.

A beverage cooler with various drinks, a snack display, and a wall with 'TREATS' signage.

A hotel lobby with a fireplace, seating area, and large windows.

A breakfast area with a sign reading 'HAPPY BREAKFAST STARTS HERE.'

4. Hampton Inn & Suites Greenfield

Greenfield

charlene

฿5,164

฿5,768 total

includes taxes & fees

30 Aug - 31 Aug

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

A modern hotel building with the name "Hotel Downtown" on the facade.

A modern interior with a large window, a wooden table, and bar stools.

5. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Victoria

฿4,729

฿5,282 total

includes taxes & fees

8 Sept - 9 Sept

A hotel lobby with a stone wall, leather chairs, a reception desk, and a sign indicating free Wi-Fi in all rooms.

A hotel room with a TV mounted on a wooden cabinet, a microwave, a coffee maker, and a desk with a chair.

A hotel room with a wooden floor, a leather sofa, a desk with a TV, a dining table with chairs, and a mirror on the wall.

A restaurant with arcade games, tables, and chairs.

6. Red Roof Inn PLUS+ South Deerfield – Amherst

South Deerfield

Katie

฿3,265

฿3,647 total

includes taxes & fees

26 Aug - 27 Aug

A fire pit with four Adirondack chairs arranged around it, overlooking a snowy landscape with distant mountains.

A hotel room with two beds, a desk, a chair, a lamp, and a view of the mountains.

A modern building with a flat roof and large windows, surrounded by a pond and trees with autumn foliage.

A large, single-story building with a red and white exterior, surrounded by green fields and a winding road.

7. Blue Vista Motor Lodge

North Adams

Frederic

฿8,139

฿8,603 total

includes taxes & fees

24 Aug - 25 Aug

A spacious kitchen with large windows, a bar area, and a dining setup with chairs and tables.

A spacious restaurant with high ceilings, patterned flooring, and multiple seating areas.

A grand chandelier with multiple candle-like lights, a white balustrade, and an arched doorway in the background.

A large, white colonial-style house with a porch, surrounded by lush greenery and trees.

8. The White House Inn

Wilmington

Eleana

฿7,771

฿8,549 total

includes taxes & fees

23 Aug - 24 Aug

A bedroom with a geometric-patterned headboard, a bed with a textured white duvet, two pillows, a bedside table with a clock, and a potted plant.

A grassy area with picnic tables and a clock tower.

A flat-screen TV mounted on a wall displaying a streaming service interface.

A large, single-story building with a central entrance and a covered walkway.

9. Windmill Motel Restaurant

Bernardston

Robert

฿4,015

฿4,484 total

includes taxes & fees

23 Aug - 24 Aug

A two-story house with a porch, a balcony, and a chimney.

A traditional dining room with a wooden table, chairs, and a chandelier.

A traditional living room with a green sofa, a yellow armchair, a wooden coffee table, and a patterned rug.

A bedroom with floral wallpaper, a bed, a dresser, a vanity, a chair, and a window with curtains.

10. Blooming Inn

Shelburne Falls

Annette

฿2,994

฿4,967 total

includes taxes & fees

8 Sept - 9 Sept

A wooden cabin with a thatched roof, accessible via a wooden walkway with railings.

A rustic wooden cabin with a thatched roof, a stone wall, and a wooden staircase leading to a balcony.

A wooden interior with a fireplace, a staircase, and a dining area.

A cozy room with a wooden wall, a red sofa, a small table with a bottle, a book, and a plant.

11. Vikings Villages Resort

Guilford

Juli

฿4,556

฿5,314 total

includes taxes & fees

13 Sept - 14 Sept

A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.

A gazebo with a red roof and white walls, surrounded by trees and a brick building.

A brick building with a red awning and a sign that reads "The Inn."

A conference table set for a meeting with chairs and folded red napkins.

12. The Inn At Crumpin Fox

Bernardston

allisha

฿5,366

฿5,994 total

includes taxes & fees

31 Aug - 1 Sept

A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

A single-story building with a porch, a chimney, and a satellite dish.

A room with a door, a table with a chair, a window with blinds, and an air conditioning unit.

A reception desk with a computer, a monitor, and a sign about Choice Privileges.

13. Rodeway Inn

Adams

Andrew

฿2,379

฿2,657 total

includes taxes & fees

26 Aug - 27 Aug

A building with a covered parking area and a grassy front yard.

A dining area with wooden chairs and tables, a kitchen counter with appliances, and framed pictures on the wall.

A hotel room with a large bed, two bedside tables with lamps, a desk with a chair, and a small window.

A rectangular swimming pool with a wooden deck surrounding it.

14. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

฿3,304

฿3,690 total

includes taxes & fees

20 Aug - 21 Aug

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

A hotel room with two blue upholstered chairs, a wooden table with a lamp, a TV mounted on the wall, and a wooden dresser with drawers.

A white two-story building with a porch, labeled as a motel.

A hay bale display with pumpkins and scarecrows.

15. Willows Motel Williamstown

Williamstown

Richard

฿3,422

฿3,822 total

includes taxes & fees

23 Aug - 24 Aug

A neatly arranged hotel room with a bed, a chair, a desk, and two framed pictures on the wall.

A wooden sign with 'RESTAURANT RECEPTION ENTRANCE' and an arrow pointing right.

A hotel room with a bed, a chair, a lamp, and a window with curtains.

A living room with a sofa, a coffee table, a television, a fireplace, a cabinet, and a lamp.

16. Deerfield Inn

Deerfield

Jonathan

฿8,166

฿10,574 total

includes taxes & fees

20 Aug - 21 Aug

A reception area with a counter, a computer, and various informational posters on the wall.

A motel with a central staircase, multiple rooms, and a parking lot.

A bathroom with a toilet, sink, and bathtub.

A hotel room with a bed, bedside table, lamp, and a mirror.

17. Travelodge by Wyndham Brattleboro VT

Brattleboro

Jessica

฿2,052

฿2,257 total

includes taxes & fees

27 Aug - 28 Aug

A living room with a fireplace, two sofas, and four black side tables.

A bedroom with a bed, a sofa, a fireplace, and a chandelier.

A two-story building with a symmetrical facade, large columns, and a central entrance.

A dining area with a wooden table, four chairs, and a framed picture on the wall.

18. The Revival House

Adams

James

฿5,472

฿6,112 total

includes taxes & fees

20 Aug - 21 Aug

A cozy living room with a fireplace, a coffee station, and a view of the outside.

A hotel room with two beds, a desk, a chair, a television, a dresser, and a door leading to a bathroom.

A dining table with a vase of flowers, a chair, and a window with a view.

A motel with multiple floors, each with balconies and windows.

19. Colonial Motel

Brattleboro

James

฿2,715

฿2,987 total

includes taxes & fees

1 Sept - 2 Sept

A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.

A room with a dining table, chairs, a sofa, and a red carpet leading to a door.

A sunroom with large windows, a dining area with a table and chairs, and a sofa.

A hotel lobby with a red carpet, a reception desk, a sofa, and chairs.

20. Econo Lodge Brattleboro South

Brattleboro

Edgardo

฿2,944

฿3,238 total

includes taxes & fees

26 Aug - 27 Aug

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Stay near popular Charlemont attractions

An old wooden covered bridge surrounded by autumn foliage.

Bissell Covered Bridge

This historic wooden bridge spans Mill Brook, showcasing 19th-century craftsmanship in a serene natural setting. Autumn visitors are rewarded with spectacular foliage framing the 92-foot structure.

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A wooden boardwalk through a forest with snow patches and bare trees.

Hawley Bog Preserve

This rare New England bog features a floating peat mat with carnivorous plants and rare orchids. Walk the 700-foot boardwalk through this delicate ecosystem for close encounters with unique botanical treasures.

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Berkshire East Ski Resort

8.8/10 (57 reviews)

This eco-pioneer ski resort powers itself entirely through on-site wind and solar energy. Experience 45 diverse trails in winter or North America's longest zip lines and alpine coaster in summer.

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Zoar Outdoor/Deerfield Valley Canopy Tours

10.0/10 (1 review)

Soar through the Berkshires on New England's first zip line canopy tour, featuring 11 thrilling lines and sky bridges. The three-hour adventure offers unique aerial views of the Deerfield River Valley's diverse forests.

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Thunderbolt Mountain Coaster

Plunge through the Berkshire Mountains on North America's longest mountain coaster, controlling your own speed. Soar around 360° turns and rolling drops while taking in breathtaking panoramic forest views.

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Charlemont Federated Church

This welcoming congregation embodies progressive Christian values through inclusive services and community outreach. Experience their spiritual warmth at 9:30am worship or join their Good Neighbors Food Pantry initiative.

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Hail to the Sunrise Statue

This bronze tribute to Native American heritage stands with arms outstretched to greet the rising sun. Visit at dawn when morning light illuminates the statue and reflecting pool with inscribed tribal stones.

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West Branch Wildlife Sanctuary

This 1,814-acre sanctuary protects rare plants and diverse wildlife within the Wild & Scenic Westfield River watershed. Explore the trail through hardwood forests and hemlock stands for exceptional birdwatching.

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Learn more about Charlemont

Nestled in the Berkshires, this outdoor enthusiast's paradise offers thrilling whitewater rafting on the Deerfield River and scenic zip-lining adventures. Nearby, Mohawk Trail State Forest beckons hikers with its old-growth trees, while Berkshire East Mountain Resort provides year-round activities from skiing to mountain biking.

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Top Charlemont Hotel Reviews

Hampton Inn Brattleboro

10/10 Excellent

"The facility was clean, comfortable and friendly staff"

Howard Johnson by Wyndham Lenox

8/10 Good

"The motel is in a great location. You could walk to everything. The room was clean and comfortable although the air conditioning in the room didn't work very well. The fan ran but it didn't cool the room."

Vacation Village in the Berkshires

10/10 Excellent

"This is a great resort with large, clean, well equipped rooms. My only gripe is the location is quite remote and you have to drive 10 minutes for food."

The Williams Inn

10/10 Excellent

"Our stay at The Williams Inn was amazing. The rooms were clean and beautiful, the staff was helpful and friendly, and our overall experience was superb. Would recommend 100%!"

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Having the pool and hot tub was great. Very clean. Breakfast was complete with oatmeal and hot breakfast choices. Location was Central to all sites like Tanglewood. Highly recommended."

Hotel UMass

8/10 Good

"The property is beautiful, well kept, and clean. It is difficult to find the place because it is in the middle of UMASS campus. The signage needs improvement. It is a long walk from the parking lot to the lobby. Once you have the location and parking figure out, the place is great."

Jiminy Peak Mountain Resort

10/10 Excellent

"…."

Hotel On North

10/10 Excellent

"A great location for a concert at Tanglewood and a chance to explore a new city. Parking is easy and convenient. The staff is very welcoming and helpful. The facilities are clean, modern, quiet, and vintage at the same time. A beautiful bar and restaurant on site and many restaurants and coffee shops in walking distance. I would definitely stay here again!"

The Yankee Inn

8/10 Good

"The stay was very good however the rooms are dated though well maintained. I felt the price was very high for the accommodations. I had expected more for the price ($350) but it was their peak season and they need to price accordingly. Certainly this Inn did not offer the feel or quality level of even a Holiday Inn or Hampton Inn. That being said it was very clean, the staff was very friendly and the breakfast was good."

More cheap stays in Charlemont