Ashuwillticook Rail Trail Holiday Houses

Ashuwillticook Rail Trail Holiday Homes
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A paved path flanked by trees with autumn foliage, a wooden fence, and a clear blue sky.

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Our top choices for Ashuwillticook Rail Trail holiday homes

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

A small, single-story house with a porch, surrounded by a well-maintained lawn and trees.

A living room with a floral sofa, a black leather chair, a small table, and a patterned rug.

A kitchen with wooden cabinets, a stainless steel refrigerator, a gas stove, and a built-in oven.

1. Cozy Home in Pownal VT

Cozy Home in Pownal VT

Pownal

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."

Jess M.

The price is NZ$366

NZ$366

includes taxes & fees

8 Oct - 9 Oct

Cozy Home in Pownal VT

A kitchen with a central island, a built-in sink, and a ceiling fan.

A wooden deck with two Adirondack chairs and a railing, surrounded by trees with autumn foliage.

A kitchen with wooden cabinets, a microwave, stove, and a bar area with wooden chairs.

2. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock

8.4 out of 10, Very good, (10 reviews)

8.4/10

Very good

(10 reviews)

"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."

Maura L.

The price is NZ$962

NZ$962

includes taxes & fees

4 Oct - 5 Oct

Comfortable Berkshires retreat on mtn resort, SISO

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

A compact kitchen with a dining table and chairs, a microwave, and a refrigerator.

A living room with two grey sofas, a wooden coffee table, a painting on the wall, and a lamp.

3. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

8.6 out of 10, Excellent, (7 reviews)

8.6/10

Excellent

(7 reviews)

"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"

Varun M.

The price is NZ$367

NZ$367

includes taxes & fees

4 Oct - 5 Oct

NEW RENO - Chalet-style farm loft near Tanglewood

A spacious living room with a dining area, a kitchen, and a large window.

A bedroom with a bed, two bedside tables, a window, a skylight, and a door leading outside.

A kitchen with white cabinets, a wooden dining table, and a large window.

A gazebo with a stone floor and a grassy area with trees in the background.

4. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

7.0 out of 10, Good, (2 reviews)

7.0/10

Good

(2 reviews)

"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"

Leslie H.

The price is NZ$403

NZ$403

includes taxes & fees

5 Oct - 6 Oct

1800s Carriage house in Berkshires / Hudson Valley

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

A wooden deck with a bench and umbrella, a door, and a window.

A spacious kitchen with a large island, built-in appliances, and a laundry area.

A modern living room with a fireplace, white cabinetry, a large flat-screen TV, and a cozy seating area with patterned cushions.

5. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

9.8 out of 10, Exceptional, (7 reviews)

9.8/10

Exceptional

(7 reviews)

"The host was extremely communicative and went above and beyond to ensure guest comfort."

Diego G.

The price is NZ$1,012

NZ$1,012

includes taxes & fees

5 Oct - 6 Oct

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

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

A cozy room with a wooden bench, a small table, and a chair.

A room with a wooden bench, a table, and a door with glass panels.

A narrow hallway with a wooden floor, a black door at the end, and a wall with floral wallpaper.

6. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA

North Adams

10.0 out of 10, Exceptional, (61 reviews)

10/10

Exceptional

(61 reviews)

"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."

Diane

The price is NZ$863

NZ$863

includes taxes & fees

13 Oct - 14 Oct

A roomy remodeled retreat close to MassMoCA

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

A modern kitchen with a dining area, a sofa, and a bookshelf.

A modern living room with a sofa, a round mirror, two floor lamps, a vase with green plants, and a small round table with a book.

A bedroom with a large bed, a window, and a chandelier.

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

Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Williamstown

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "

Michelle B.

The price is NZ$1,102

NZ$1,102

includes taxes & fees

19 Oct - 20 Oct

Walk to Williams * Steam Sauna * Ritz-Carlton Bed

A wooden deck with a table and chairs, surrounded by a white railing.

A residential area with houses, a driveway, and a body of water in the background.

A bedroom with a bed, a ceiling fan, a window with curtains, and a framed picture on the wall.

A modern kitchen with grey cabinets, a black refrigerator, a microwave, and a dishwasher.

8. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

8.4 out of 10, Very good, (10 reviews)

8.4/10

Very good

(10 reviews)

"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."

Stephen L.

The price is NZ$883

NZ$883

includes taxes & fees

13 Oct - 14 Oct

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

A kitchen with wooden cabinets, a microwave, a stove, and a refrigerator. There are bar stools and a book on the counter.

A red building with a stone wall, a wooden deck, and a gravel path leading to the entrance.

A bedroom with a bed, a bench, a chair, a nightstand, a table, and a ceiling fan.

9. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"Very good trip overall. Great location. Just a few things needed to make it over the top!"

William C B.

The price is NZ$542

NZ$542

includes taxes & fees

5 Oct - 6 Oct

Real Estate: Therapy - Lake, Laundry, Love it

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

An outdoor seating area with a wooden table and chairs, a small fire pit, and string lights.

A modern kitchen with wooden floors, stainless steel appliances, and grey cabinets.

A cozy cabin interior with a stone fireplace, wooden walls, and a sofa in the living area.

10. Greylock Cabin

Greylock Cabin

Florida

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"

Margaret M.

The price is NZ$813

NZ$813

includes taxes & fees

29 Oct - 30 Oct

Greylock Cabin

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

A cozy living room with a grey sofa, a patterned throw blanket, and a wooden ceiling.

A triangular-shaped building with a balcony and a wooden picnic table in front.

A cabin in a forest with a dirt path leading to it, surrounded by trees.

11. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

Sharon K.

The price is NZ$678

NZ$678

includes taxes & fees

7 Oct - 8 Oct

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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

A cozy cabin interior with a dining area, sofa, fireplace, and a television.

A modern living room with a flat-screen TV, wooden flooring, a gray sofa, and a kitchen in the background.

A cozy cabin interior with a sectional sofa, a coffee table, a small cabinet, and a window with a view of the outdoors.

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

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

Woodford

The price is NZ$825

NZ$825

includes taxes & fees

7 Oct - 8 Oct

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

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

A cozy living room with a green sofa, a patterned armchair, a wooden coffee table, and a bookshelf.

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

A grassy outdoor area with a seating arrangement.

13. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "

Christine C.

The price is NZ$880

NZ$880

includes taxes & fees

7 Oct - 8 Oct

1789 Shaker Farmhouse in Berkshires/Hudson Valley

A hot tub with a string of lights above it, set against a dark night sky.

A living room with a ceiling fan, a TV, a sofa, a chair, and a rug.

A bedroom with a bed, bedside lamps, a window with curtains, a ceiling light, and a framed picture on the wall.

A rustic cabin with a gravel path leading to a bench in a forested area.

14. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

9.8 out of 10, Exceptional, (17 reviews)

9.8/10

Exceptional

(17 reviews)

"Great place and welcoming stay!"

Frank M.

The price is NZ$700

NZ$700

includes taxes & fees

14 Oct - 15 Oct

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

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

A bedroom with a bed, a nightstand, a lamp, a ceiling fan, and two windows.

A wooden-floored hallway with a door, a window, and a chandelier.

A two-story house with a front porch, a flag, and a snow-covered driveway.

15. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain

Charlemont

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "

Jason F.

The price is NZ$1,221

NZ$1,221

includes taxes & fees

6 Oct - 7 Oct

5BR Berkshire Home Mins To The Mountain

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

A modern kitchen with wooden cabinets, a central island, a refrigerator, a sink, and pendant lighting.

A wooden cabinet with multiple compartments, including glass doors and drawers, likely used for storage.

A large white house with black shutters, surrounded by snow-covered trees and a fence.

16. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock

10.0 out of 10, Exceptional, (22 reviews)

10/10

Exceptional

(22 reviews)

"Amazing Inn. Cozy and everything we needed. "

Price F.

The price is NZ$2,051

NZ$2,051

includes taxes & fees

6 Oct - 7 Oct

Hancock Village Inn Near Jiminy Peak

A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

A bedroom with a bed, bedside lamp, and a window with curtains.

A modern kitchen with built-in appliances, wooden cabinets, and a herringbone floor pattern.

A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

17. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!

Richmond

The price is NZ$1,208

NZ$1,208

includes taxes & fees

6 Oct - 7 Oct

Ellie’s Overlook, best view in the Berkshires!

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

A backyard with a campfire, two Adirondack chairs, and a house in the background.

A cozy living room with a beige sofa, a wooden coffee table, and two lamps.

A kitchen with white cabinets, a granite countertop, and a door leading to another room.

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

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

Whitingham

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"Great 2 family group vacation spot. Very clean and right in between great ski mountains"

Jonathan

The price is NZ$971

NZ$971

includes taxes & fees

28 Oct - 29 Oct

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

A living room with a sofa, armchairs, a coffee table, and a television.

A dining area with a wooden table, white chairs, and a hanging light fixture.

A rustic wooden building with a chimney, surrounded by lush greenery and flowering plants.

19. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."

Patricia O.

The price is NZ$1,212

NZ$1,212

includes taxes & fees

19 Oct - 20 Oct

Sun Filled Lenox Retreat - Minutes to Tanglewood!

A modern living room with a sofa, armchair, coffee table, and TV.

A kitchen with white brick backsplash, stainless steel appliances, wooden cabinets, and a wooden island.

A porch with a bench, a potted plant, and a black door with the number 175.

A living room with a sofa, armchair, coffee table, and a staircase leading to another room.

20. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups

Lee

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"This older home was beautifully renovated and was able to easily accommodate our large group."

Beth S.

The price is NZ$1,032

NZ$1,032

includes taxes & fees

5 Oct - 6 Oct

Spacious Central Berkshires Home for Groups

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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Ashuwillticook Rail Trail Holiday Homes information

Number of reviews	193
Accommodation	0 Holiday Homes
Lowest Price	NZ$366
Highest Price	NZ$2,051

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Book Holiday Homes in Ashuwillticook Rail Trail on Expedia.com

Holiday Homes in Ashuwillticook Rail Trail

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ashuwillticook Rail Trail holiday homes

1. Cozy Home in Pownal VT

2. Comfortable Berkshires retreat on mtn resort, SISO

3. NEW RENO - Chalet-style farm loft near Tanglewood

4. 1800s Carriage house in Berkshires / Hudson Valley

5. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

6. A roomy remodeled retreat close to MassMoCA

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

8. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

9. Real Estate: Therapy - Lake, Laundry, Love it

10. Greylock Cabin

11. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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

13. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

14. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

15. 5BR Berkshire Home Mins To The Mountain

16. Hancock Village Inn Near Jiminy Peak

17. Ellie’s Overlook, best view in the Berkshires!

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

19. Sun Filled Lenox Retreat - Minutes to Tanglewood!

20. Spacious Central Berkshires Home for Groups

Find holiday rentals that suit your style

Top Ashuwillticook Rail Trail Hotel Reviews

Find out more about Ashuwillticook Rail Trail

Ashuwillticook Rail Trail Holiday Homes information

Explore a world of travel with Expedia