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

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60 Best Family Vacation Rentals in Lanesborough (Starting from $206)

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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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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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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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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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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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
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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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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
Check Availability
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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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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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
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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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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
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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
Check Availability
Lakeside Berkshires Home Near Hiking & Skiing!
Lakeside Berkshires Home Near Hiking & Skiing!
House
Lanesborough, MA, 01237, United States
4.3k from Lanesborough center

Balcony, Crib, Dryer, Extra Bed, Free Parking, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms7 Guests
8.8

Fabulous

5 reviews

$500
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
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A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Cabin
Pittsfield, MA, 01201, United States
4.4k from Lanesborough center

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

2 Bedrooms5 Guests
10.0

Exceptional

129 reviews

$307
Average price / night
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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
Lakefront Home on Pontoosuc Lake, the Berkshires
Lakefront Home on Pontoosuc Lake, the Berkshires
House
Lanesborough, MA, 01237, United States
4.6k from Lanesborough center

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

3 Bedrooms8 Guests
9.2

Superb

5 reviews

$476
Average price / night
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Ray of Sunshine Berkshire Home on Pontoosuc Lake
Ray of Sunshine Berkshire Home on Pontoosuc Lake
House
Pittsfield, MA, 01201, United States
4.8k from Lanesborough center

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

5 Bedrooms14 Guests
10.0

Exceptional

15 reviews

$851
Average price / night
Check Availability
19th c. Barn in the Berkshires
19th c. Barn in the Berkshires
House
Cheshire, MA, 01225, United States
4.9k from Lanesborough center

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

3 Bedrooms9 Guests
9.6

Exceptional

95 reviews

$414
Average price / night
Check Availability
Lake Views & Dock Access - Pittsfield Cottage!
Lake Views & Dock Access - Pittsfield Cottage!
Cottage
Pittsfield, MA, 01201, United States
5.0k from Lanesborough center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Living Area

4 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$497
Average price / night
Check Availability
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
House
Lanesborough, MA, 01237, United States
5.1k from Lanesborough center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, Outdoor Space

1 Bedroom2 Guests
9.8

Exceptional

277 reviews

$206
Average price / night
Check Availability
Berkshire Lake Beauty-Modern Amenities On The Lake
Berkshire Lake Beauty-Modern Amenities On The Lake
House
Pittsfield, MA, 01201, United States
5.4k from Lanesborough center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

5 Bedrooms14 Guests
10.0

Exceptional

112 reviews

$595
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 Family Vacation Rentals in Lanesborough.

Lanesborough Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 60 verified family-friendly vacation rentals in Lanesborough. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Lanesborough vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $206 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Lanesborough offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Lanesborough are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Lanesborough often include amenities such as Child Friendly, Fireplace/Heating, and Internet. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.