Vacation Rentals in Lanesborough, MA: Compare 10+ Sites & Save

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112 Best Vacation Rentals in Lanesborough (Starting from $191)

Lakeside Berkshires Home Near Hiking and Skiing!
Lakeside Berkshires Home Near Hiking and Skiing!
House
Lanesborough, MA, USA
4.3k from Lanesborough center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms7 Guests
New to Booking
$471
Average price / night
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Charming historic cottage on scenic road to Mt. Greylock
Charming historic cottage on scenic road to Mt. Greylock
Cottage
Lanesboro, MA, 01237, United States
0.4k from Lanesborough center

AC, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, Toys

2 Bedrooms5 Guests
10.0

Exceptional

118 reviews

$227
Average price / night
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Lake Views and Dock Access - Pittsfield Cottage!
Lake Views and Dock Access - Pittsfield Cottage!
House
Pittsfield, MA, USA
5.0k from Lanesborough center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms6 Guests
New to Booking
$552
Average price / night
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Mountain Blossom Retreat by Evergreen Home
Mountain Blossom Retreat by Evergreen Home
House
Lanesborough, MA, 01237, United States
0.5k from Lanesborough center

AC, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater

3 Bedrooms8 Guests
10.0

Exceptional

10 reviews

$879
Average price / night
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Family-Friendly Hancock Home Walk to Slopes!
Family-Friendly Hancock Home Walk to Slopes!
House
Hancock, MA, USA
5.4k from Lanesborough center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

4 Bedrooms15 Guests
New to Booking
$1320
Average price / night
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Bright Boho Apt in 18th c Berkshire Farmhouse
Bright Boho Apt in 18th c Berkshire Farmhouse
Apartment
Lanesborough, MA, 01237, United States
0.7k from Lanesborough center

AC, Extra Bed, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

1 Bedroom4 Guests
9.0

Fabulous

22 reviews

$191
Average price / night
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Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort
Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort
House
Hancock, MA, USA
5.4k from Lanesborough center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms10 Guests
8.5

Very Good

10 reviews

$618
Average price / night
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Cozy Cottage in Berkshires: Minutes to Jiminy Peak
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
House
Lanesborough, MA, 01237, United States
2.2k from Lanesborough center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$381
Average price / night
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half Mi to Jiminy Peak Condo with Pool and Hot Tub
half Mi to Jiminy Peak Condo with Pool and Hot Tub
Apartment
Hancock, MA, USA
5.5k from Lanesborough center

Apartments, Accommodations, Parking, Lodgings, Hot tubs, Places to stay, Ski resorts, Condos

2 Bedrooms4 Guests
New to Booking
$331
Average price / night
Check Availability
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
House
Lanesborough, MA, 01237, United States
2.9k from Lanesborough center

Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms14 Guests
9.8

Exceptional

29 reviews

$971
Average price / night
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Walk to Ski Slopes Jiminy Peak Resort Getaway!
Walk to Ski Slopes Jiminy Peak Resort Getaway!
Apartment
Hancock, MA, USA
5.6k from Lanesborough center

Apartments, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Ski resorts

3 Bedrooms8 Guests
New to Booking
$634
Average price / night
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Hearts Desire is your private escape.
Hearts Desire is your private escape.
House
Lanesborough, MA, 01237, United States
3.0k from Lanesborough center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
10.0

Exceptional

105 reviews

$281
Average price / night
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Mountain View Suite on Jiminy Peak Ski On Off -New
Mountain View Suite on Jiminy Peak Ski On Off -New
Apartment
Hancock, MA, USA
5.8k from Lanesborough center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Ski resorts

1 Bedroom4 Guests
9.4

Superb

19 reviews

$335
Average price / night
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Breathtaking Post & Beam minutes from Jiminy Peak, Williamstown, Lenox & hiking
Breathtaking Post & Beam minutes from Jiminy Peak, Williamstown, Lenox & hiking
House
Lanesborough, MA, 01237, United States
3.3k from Lanesborough center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

4 Bedrooms12 Guests
10.0

Exceptional

16 reviews

$893
Average price / night
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1st Floor Mountain View Suite Ski On Off At Jiminy- Fully Redone Decor
1st Floor Mountain View Suite Ski On Off At Jiminy- Fully Redone Decor
Apartment
Hancock, MA, USA
5.8k from Lanesborough center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Ski resorts

1 Bedroom4 Guests
7.7

Good

6 reviews

$335
Average price / night
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New Custom Home Meets Nature’s Splendor in This Stunning Berkshires Retreat
New Custom Home Meets Nature’s Splendor in This Stunning Berkshires Retreat
House
Lanesborough, MA, 01237, United States
3.4k from Lanesborough center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$499
Average price / night
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Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor
Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor
Apartment
Hancock, MA, USA
5.8k from Lanesborough center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$335
Average price / night
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Berkshires Lakefront Retreat by Evergreen Home
Berkshires Lakefront Retreat by Evergreen Home
House
Cheshire, MA, 01225, United States
3.5k from Lanesborough center

AC, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$744
Average price / night
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Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Apartment
Hancock, MA, USA
5.8k from Lanesborough center

Apartments, Cheap, Accommodations, Pools, Lodgings, Places to stay, Family, Ski resorts

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$279
Average price / night
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Wildlife Lakeside Cottage\nbeautiful views, amazing wildlife, great location
Wildlife Lakeside Cottage\nbeautiful views, amazing wildlife, great location
House
Lanesborough, MA, 01224, United States
3.9k from Lanesborough center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.6

Exceptional

76 reviews

$372
Average price / night
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Cozy Ski in out Cabin in Berkshire Resort
Cozy Ski in out Cabin in Berkshire Resort
House
Hancock, MA, USA
5.8k from Lanesborough center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cabins, Cottages, Pet-friendly

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$323
Average price / night
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Berkshire 6BR Estate • Pool, Hot Tub, Game Room
Berkshire 6BR Estate • Pool, Hot Tub, Game Room
House
Lanesborough, MA, 01237, United States
4.0k from Lanesborough center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub

6 Bedrooms14 Guests
10.0

Exceptional

13 reviews

$997
Average price / night
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Disney Wonderland Suite at Jiminy-Ski On Off Mtn - Must See Stitch and Mickey Magic
Disney Wonderland Suite at Jiminy-Ski On Off Mtn - Must See Stitch and Mickey Magic
Apartment
Hancock, MA, USA
5.8k from Lanesborough center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay, Family, Ski resorts

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$252
Average price / night
Check Availability
Cheshire Cove | Waterfront • Kayak • Firepit
Cheshire Cove | Waterfront • Kayak • Firepit
House
Cheshire, MA, 01225, United States
4.0k from Lanesborough center

Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
New to Booking
$354
Average price / night
Check Availability
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Apartment
Hancock, MA, USA
5.8k from Lanesborough center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay, Family, Ski resorts

1 Bedroom4 Guests
9.2

Superb

5 reviews

$252
Average price / night
Check Availability
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
House
Hancock, MA, 01237, United States
4.0k from Lanesborough center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
9.8

Exceptional

71 reviews

$388
Average price / night
Check Availability
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
House
Lanesborough, MA, 01237, United States
4.2k from Lanesborough center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms7 Guests
9.8

Exceptional

13 reviews

$465
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Lanesborough.

Lanesborough Vacation Rentals on the Map

Frequently Asked Questions

You can explore 112 verified vacation rentals in Lanesborough. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Lanesborough vary depending on the season, property size, and location. Rates typically start from around $191 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Lanesborough include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Lanesborough welcome pets. Currently, 14 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Lanesborough often include amenities such as Fireplace/Heating, Internet, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.