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Holiday Homes in Lanesborough

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Lanesborough holiday homes

A heated pool

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)
"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."
United States
Maura L.
The price is AU$784
includes taxes & fees
19 Aug - 20 Aug
Comfortable Berkshires retreat on mtn resort, SISO
Outdoor dining

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)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AU$776
includes taxes & fees
19 Aug - 20 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Coffee/tea maker, fridge, microwave, oven

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)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is AU$295
includes taxes & fees
19 Aug - 20 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
Coffee/tea maker, fridge, microwave, stovetop

4. 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, (6 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AU$796
includes taxes & fees
24 Aug - 25 Aug
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
TV, DVD player, books, video library

5. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 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)"
United States
Leslie H.
The price is AU$340
includes taxes & fees
14 Sept - 15 Sept
1800s Carriage house in Berkshires / Hudson Valley
Pool

6. Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (76 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Dining

7. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (6 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is AU$291
includes taxes & fees
20 Aug - 21 Aug
Cozy Home in Pownal VT
Outdoor dining

8. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AU$1,579
includes taxes & fees
9 Sept - 10 Sept
Hancock Village Inn Near Jiminy Peak
Exterior

9. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 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. "
United States
Christine C.
The price is AU$842
includes taxes & fees
8 Sept - 9 Sept
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Smart TV

10. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (4 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AU$555
includes taxes & fees
14 Sept - 15 Sept
stylish Berkshires Retreat
Exterior

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

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (35 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Interior

12. 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, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$561
includes taxes & fees
9 Sept - 10 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Outdoor spa tub

13. 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, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$557
includes taxes & fees
25 Aug - 26 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AU$430
includes taxes & fees
13 Sept - 14 Sept
Real Estate: Therapy - Lake, Laundry, Love it
Dining

15. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (58 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is AU$661
includes taxes & fees
9 Sept - 10 Sept
A roomy remodeled retreat close to MassMoCA
Exterior

16. North Getaway Cottage

North Getaway Cottage
Williamstown
8.8 out of 10, Excellent, (27 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is AU$653
includes taxes & fees
31 Aug - 1 Sept
North Getaway Cottage
Dining

17. 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)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is AU$818
includes taxes & fees
16 Sept - 17 Sept
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Property grounds

18. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Stamford
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful area and views of mountains, very gracious host "
United States
Donna E.
The price is AU$464
includes taxes & fees
24 Aug - 25 Aug
Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Property grounds

19. Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (5 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is AU$645
includes taxes & fees
28 Aug - 29 Aug
Riverbend Berkshire East Basecamp - 3 bedrooms available
Interior

20. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AU$456
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat
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

The Yankee Inn

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."
Gary 1-night trip
Posted less than an hour ago
The Yankee Inn

Find out more about Lanesborough

Lanesborough Holiday Homes information

Number of reviews
248
Accommodation
303 Holiday Homes
Lowest Price
AU$291
Highest Price
AU$1,579