Family-Friendly Vacation Rentals in Hancock Shaker Village, MA: Compare 10+ Sites & Save

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58 Best Family Vacation Rentals in Hancock Shaker Village (Starting from $109)

1 Mi to Vineyard Serene Berkshires Country Escape
1 Mi to Vineyard Serene Berkshires Country Escape
House
Richmond, MA, USA
4.3k from Hancock Shaker Village center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom7 Guests
New to Booking
$497
Average price / night
Check Availability
Friendly Hills | Passive Home • EV Charger
Friendly Hills | Passive Home • EV Charger
House
Pittsfield, MA, 01201, United States
0.3k from Hancock Shaker Village center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$488
Average price / night
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Historic New Lebanon Hideaway on 33 Private Acres!
Historic New Lebanon Hideaway on 33 Private Acres!
House
NY, USA
4.7k from Hancock Shaker Village center

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

5 Bedrooms10 Guests
8.0

Good

2 reviews

$623
Average price / night
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Berkshires Colonial on 2 Acres by Evergreen Home
Berkshires Colonial on 2 Acres by Evergreen Home
House
Pittsfield, MA, 01201, United States
1.8k from Hancock Shaker Village center

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

4 Bedrooms10 Guests
10.0

Exceptional

7 reviews

$458
Average price / night
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Berkshire Mountain Lodge
Berkshire Mountain Lodge
Cabin
Pittsfield, MA, USA
6.8k from Hancock Shaker Village center

Accommodations, Pools, Parking, Lodges, Cabins, 4-star, Lodgings, Hot tubs, Places to stay

4 Bedrooms8 Guests
8.3

Very Good

660 reviews

$285
Average price / night
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Family Fun in The Berkshires at Beautiful Hygge House
Family Fun in The Berkshires at Beautiful Hygge House
House
Pittsfield, MA, 01201, United States
2.4k from Hancock Shaker Village center

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

3 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$526
Average price / night
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Beautiful Lenox Home, 3 Mi to Shakespeare and Co!
Beautiful Lenox Home, 3 Mi to Shakespeare and Co!
House
Lenox, MA, USA
7.4k from Hancock Shaker Village center

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

3 Bedrooms6 Guests
9.0

Fabulous

3 reviews

$253
Average price / night
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Modern 4 bedroom lakefront house in The Berkshires.
Modern 4 bedroom lakefront house in The Berkshires.
House
Pittsfield, MA, 01201, United States
2.6k from Hancock Shaker Village center

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

4 Bedrooms8 Guests
10.0

Exceptional

99 reviews

$646
Average price / night
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Spacious Historic Home in the Berkshires!
Spacious Historic Home in the Berkshires!
House
Pittsfield, MA, USA
7.6k from Hancock Shaker Village center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

5 Bedrooms9 Guests
New to Booking
$261
Average price / night
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Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
House
Pittsfield, MA, 01201, United States
3.0k from Hancock Shaker Village center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
9.6

Exceptional

104 reviews

$315
Average price / night
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Elegant Pittsfield Home Near Downtown and Skiing!
Elegant Pittsfield Home Near Downtown and Skiing!
House
Pittsfield, MA, USA
7.7k from Hancock Shaker Village center

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

5 Bedrooms10 Guests
9.7

Exceptional

3 reviews

$947
Average price / night
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20 minutes to Jiminy Peak and Bousquet Mountain
20 minutes to Jiminy Peak and Bousquet Mountain
Cottage
New Lebanon, NY, 12125, United States
3.4k from Hancock Shaker Village center

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

2 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$313
Average price / night
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Restored 1881 Farm House
Restored 1881 Farm House
House
Hancock Shaker Village, Pittsfield, Massachusetts, USA
8.8k from Hancock Shaker Village center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

4 Bedrooms4 Guests
9.5

Superb

2 reviews

$399
Average price / night
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Wellspring by AvantStay Indoor Pool Views
Wellspring by AvantStay Indoor Pool Views
House
Richmond, MA, USA
9.0k from Hancock Shaker Village center

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

1 Bedroom12 Guests
New to Booking
$960
Average price / night
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Richmond Ranch w/ Hot Tub by Evergreen Home
Richmond Ranch w/ Hot Tub by Evergreen Home
House
Richmond, MA, 01254, United States
4.1k from Hancock Shaker Village center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$344
Average price / night
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Urban Peak Escape
Urban Peak Escape
Apartment
Lenox, MA, USA
9.3k from Hancock Shaker Village center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Self-catering

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$585
Average price / night
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6 Mi to Tanglewood Peaceful Berkshire Apt!
6 Mi to Tanglewood Peaceful Berkshire Apt!
Apartment
Richmond, MA, USA
9.5k from Hancock Shaker Village center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$300
Average price / night
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Guesthouse & Permaculture Sanctuary in the Berkshires
Guesthouse & Permaculture Sanctuary in the Berkshires
House
Canaan, NY, 12029, United States
4.7k from Hancock Shaker Village center

AC, Crib, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area

7 Bedrooms14 Guests
New to Booking
$1637
Average price / night
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Walk to Dining Downtown Lenox Guest House!
Walk to Dining Downtown Lenox Guest House!
House
Lenox, MA, USA
9.6k from Hancock Shaker Village center

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

3 Bedrooms6 Guests
9.4

Superb

8 reviews

$217
Average price / night
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Tranquil Lake House Getaway on Onota Lake
Tranquil Lake House Getaway on Onota Lake
House
Pittsfield, MA, 01201, United States
5.4k from Hancock Shaker Village center

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

5 Bedrooms10 Guests
10.0

Exceptional

86 reviews

$716
Average price / night
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Perfect for Winter Skiing!!
Perfect for Winter Skiing!!
Condo
Pittsfield, MA, 01201, United States
5.8k from Hancock Shaker Village center

AC, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$706
Average price / night
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Featured in a Home & Garden TV Special 30 South Mountain Road
Featured in a Home & Garden TV Special 30 South Mountain Road
House
Pittsfield, MA, 01201, United States
6.8k from Hancock Shaker Village center

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

2 Bedrooms4 Guests
9.8

Exceptional

92 reviews

$335
Average price / night
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Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
House
Richmond, MA, 01254, United States
6.9k from Hancock Shaker Village center

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

5 Bedrooms10 Guests
10.0

Exceptional

12 reviews

$718
Average price / night
Check Availability
🌞Views! 2mi2Ski+Dtw! Great 1BR OpenLR/DR/Kit! FP,HPool,Htub,Gym,PetsOk,EVchg🌞!
🌞Views! 2mi2Ski+Dtw! Great 1BR OpenLR/DR/Kit! FP,HPool,Htub,Gym,PetsOk,EVchg🌞!
Condo
Pittsfield, MA, 01201, United States
6.9k from Hancock Shaker Village center

AC, Arcade, Barbecue, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking, Heater

1 Bedroom4 Guests
New to Booking
$214
Average price / night
Check Availability
family friendly retreat condo
family friendly retreat condo
Apartment
Pittsfield, MA, 01201, United States
7.0k from Hancock Shaker Village center

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

1 Bedroom2 Guests
New to Booking
$109
Average price / night
Check Availability
Luxury Berkshires Retreat in Lenox - Main House
Luxury Berkshires Retreat in Lenox - Main House
House
Lenox, MA, 01240, United States
7.1k from Hancock Shaker Village center

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

6 Bedrooms13 Guests
10.0

Exceptional

61 reviews

$1154
Average price / night
Check Availability
Luxury Berkshires Retreat in Lenox - Main House  & Studio
Luxury Berkshires Retreat in Lenox - Main House & Studio
House
Lenox, MA, 01240, United States
7.1k from Hancock Shaker Village center

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

8 Bedrooms17 Guests
10.0

Exceptional

55 reviews

$1387
Average price / night
Check Availability

Other accommodation types in Hancock Shaker Village:

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 Hancock Shaker Village.

Hancock Shaker Village Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 58 verified family-friendly vacation rentals in Hancock Shaker Village. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Hancock Shaker Village vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $109 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Hancock Shaker Village 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 Hancock Shaker Village 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 Hancock Shaker Village 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.