Lanesborough Holiday House Rentals from AU$298: Search Holiday Homes

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Our top choices for Lanesborough holiday homes

A two-story house with a front porch, a small garden with autumn leaves, and a clear blue sky.

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.

1. 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 AU$778

AU$778

includes taxes & fees

4 Oct - 5 Oct

Comfortable Berkshires retreat on mtn resort, SISO

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

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

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

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

2. 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 AU$698

AU$698

includes taxes & fees

13 Oct - 14 Oct

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

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

A white house with a porch, surrounded by a grassy lawn and trees with autumn foliage.

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 AU$298

AU$298

includes taxes & fees

5 Oct - 6 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 living room with a glass coffee table, a sofa, a TV, and a dining area with chairs and a table.

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 AU$329

AU$329

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

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

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 AU$819

AU$819

includes taxes & fees

5 Oct - 6 Oct

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

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.

6. 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 AU$1,608

AU$1,608

includes taxes & fees

14 Oct - 15 Oct

Hancock Village Inn Near Jiminy Peak

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

A neatly made bed with a white and light green color scheme, two bedside tables with lamps, and a window with sheer curtains.

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.

7. 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 AU$715

AU$715

includes taxes & fees

7 Oct - 8 Oct

1789 Shaker Farmhouse in Berkshires/Hudson Valley

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

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

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.

8. 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 AU$321

AU$321

includes taxes & fees

19 Oct - 20 Oct

Cozy Home in Pownal VT

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

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

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

Ellie’s Overlook, best view in the Berkshires!

Richmond

The price is AU$980

AU$980

includes taxes & fees

6 Oct - 7 Oct

Ellie’s Overlook, best view in the Berkshires!

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

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.

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

10. 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 AU$437

AU$437

includes taxes & fees

5 Oct - 6 Oct

Real Estate: Therapy - Lake, Laundry, Love it

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 house with a front porch, a large window, and a potted plant with purple flowers.

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

11. 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 AU$903

AU$903

includes taxes & fees

7 Oct - 8 Oct

Walk to Williams * Steam Sauna * Ritz-Carlton Bed

A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

A modern kitchen with a central island, stainless steel refrigerator, and pendant lighting.

A spacious living area with a wooden dining table, a black leather sofa, and a piano.

A modern living room with a leather sofa, a flat-screen TV, a fireplace, and a kitchen area visible in the background.

12. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub

New Lebanon

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "

Anonymous traveller

The price is AU$819

AU$819

includes taxes & fees

27 Oct - 28 Oct

NEW RENO Historic Creamery in Berkshires w/hot tub

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

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

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

A kitchen with white cabinets, wooden dining table, and chairs. There are hanging pendant lights and a window with a view.

13. 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 AU$681

AU$681

includes taxes & fees

13 Oct - 14 Oct

A roomy remodeled retreat close to MassMoCA

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

A kitchen with wooden cabinets, a blue countertop, and a ceiling fan. There are two bar stools and a table with papers.

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

14. 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 AU$957

AU$957

includes taxes & fees

19 Oct - 20 Oct

Sun Filled Lenox Retreat - Minutes to Tanglewood!

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 interior with a loft bed, a small kitchenette, and a welcoming 'Welcome' mat.

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.

15. 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 AU$547

AU$547

includes taxes & fees

7 Oct - 8 Oct

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

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 two-story residential house with a front porch, a small garden, and a tree with autumn leaves.

16. 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 AU$840

AU$840

includes taxes & fees

6 Oct - 7 Oct

Spacious Central Berkshires Home for Groups

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 living room with a fireplace, a sofa, a rug, and a mirror on the wall.

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

17. 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 AU$551

AU$551

includes taxes & fees

14 Oct - 15 Oct

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

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

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.

A cozy cabin interior with a kitchen, dining area, and living room.

18. 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 AU$644

AU$644

includes taxes & fees

29 Oct - 30 Oct

Greylock Cabin

A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

A small house with a deck, outdoor seating, and string lights.

A room with a white desk, two white chairs, a bookshelf, and a window with a view of trees.

A living room with a grey sectional sofa, a pink armchair, and a white coffee table. There are framed pictures on the wall and a wooden cabinet with a lamp.

19. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape

Lee

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Besides, it being in a great location, the home is absolutely lovely!"

H B.

The price is AU$1,225

AU$1,225

includes taxes & fees

18 Oct - 19 Oct

Stylish Mid-century Modern Berkshires Cape

A modern building with a wooden deck and a door.

A deck with a table and chairs, a large umbrella, and a hot tub.

A dining area with a wooden table, black wicker chairs, and a white vase. There is a painting on the wall and a ceiling light fixture.

A spacious living room with a large coffee table, two sofas, and a dining area in the background.

20. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Old Chatham

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"

Terri E.

The price is AU$878

AU$878

includes taxes & fees

5 Oct - 6 Oct

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

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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Top Lanesborough Hotel Reviews

Hotel On North

10/10 Excellent

"Delightful place with charm and warmth and character. I would love to come back."

Richard 1-night trip

Posted 3 hours ago

Hotel On North

Vacation Village in the Berkshires

10/10 Excellent

"Great place great price!"

James 1-night trip

Posted 12 hours ago

Vacation Village in the Berkshires

The Yankee Inn

8/10 Good

"Room was nice but did not have the view I was hoping for. Another hotel property is mostly blocking views from Yankee Inn looking West; the direction rooms with balcony’s face. The location near"

Theresa 2-night trip

Posted 12 hours ago

The Yankee Inn

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good

"Staff very pleasant and helpful. On site restaurant was good and reasonably priced. Room was large with a nice view. Breakfast, which is continental, seemed a bit skimpy. Plenty of parking and in a great central area with many restaurants."

Francesca 1-night trip

Posted 1 day ago

Hotel Downstreet, an Ascend Collection Hotel

Berkshires Untold

8/10 Good

"All was good for the price. Great location. Gentlemen at the bar and check-in was very pleasant and helpful. Dinner could have been better prepared."

Dan 1-night trip

Posted 1 day ago

Berkshires Untold

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

10/10 Excellent

"Most helpful staff, very clean and best breakfast around"

Sheldon 2-night trip

Posted 2 days ago

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

The Williams Inn

10/10 Excellent

"Great"

William 1-night trip

Posted 2 days ago

The Williams Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Wonderful resort"

Ofer 2-night trip

Posted 3 days ago

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn Lee - Lenox South

10/10 Excellent

"Very sweet desk clerk answered my question about late arrival quickly and cheerfully."

Chris 1-night trip

Posted 3 days ago

Quality Inn Lee - Lenox South

Find out more about Lanesborough

Lanesborough Holiday Homes information

Number of reviews	189
Accommodation	303 Holiday Homes
Lowest Price	AU$298
Highest Price	AU$1,608

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Lanesborough on Expedia.com

Holiday Homes in Lanesborough

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lanesborough holiday homes

1. Comfortable Berkshires retreat on mtn resort, SISO

2. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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. Hancock Village Inn Near Jiminy Peak

7. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

8. Cozy Home in Pownal VT

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

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

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

12. NEW RENO Historic Creamery in Berkshires w/hot tub

13. A roomy remodeled retreat close to MassMoCA

14. Sun Filled Lenox Retreat - Minutes to Tanglewood!

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

16. Spacious Central Berkshires Home for Groups

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

18. Greylock Cabin

19. Stylish Mid-century Modern Berkshires Cape

20. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Find holiday rentals that suit your style

Top Lanesborough Hotel Reviews

Hotel On North

Find out more about Lanesborough

Lanesborough Holiday Homes information

Explore a world of travel with Expedia