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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Family Vacation Rentals
  3.  USA

  4.  Massachusetts

  5.  Hancock

Refine your search

Price per night

Amenity Filter

Rating

70 Best Family Vacation Rentals in Hancock (Starting from $165)

Family-Friendly Hancock Home Walk to Slopes!
Family-Friendly Hancock Home Walk to Slopes!
House
Hancock, MA, USA
0.8k from Hancock center

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

4 Bedrooms15 Guests
New to Booking
$1320
Average price / night
Check Availability
Mountainside Condo Ski In Ski Out
Mountainside Condo Ski In Ski Out
Apartment
Hancock, MA, 01237, United States
0.7k from Hancock center

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

1 Bedroom4 Guests
9.0

Fabulous

37 reviews

$168
Average price / night
Check Availability
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
0.9k from Hancock 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
Check Availability
Mountain View Suite on Jiminy Peak Ski On Off -New
Mountain View Suite on Jiminy Peak Ski On Off -New
Apartment
Hancock, MA, USA
1.1k from Hancock 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
Check Availability
Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA
Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA
House
Hancock, MA, 01237, United States
1.0k from Hancock center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

5 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$1539
Average price / night
Check Availability
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
1.1k from Hancock 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
Check Availability
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Condo
Hancock, MA, 01237, United States
1.1k from Hancock center

AC, Arcade, Balcony, Breakfast Available, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking

3 Bedrooms10 Guests
10.0

Exceptional

43 reviews

$317
Average price / night
Check Availability
Cozy Ski in out Cabin in Berkshire Resort
Cozy Ski in out Cabin in Berkshire Resort
House
Hancock, MA, USA
1.1k from Hancock 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
Large Mountainside Condo with Private Trail to Grouse Run
Large Mountainside Condo with Private Trail to Grouse Run
Condo
Hancock, MA, 01237, United States
1.2k from Hancock center

AC, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$734
Average price / night
Check Availability
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
1.1k from Hancock 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
Ski season is here!
Ski season is here!
Condo
Hancock, MA, 01237, United States
1.2k from Hancock center

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

2 Bedrooms6 Guests
10.0

Exceptional

51 reviews

$539
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
1.1k from Hancock 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
Ski-In/Ski-Out at Jiminy Peak  in the Country Inn
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Condo
Hancock, MA, 01201, United States
1.2k from Hancock center

AC, Arcade, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

1 Bedroom4 Guests
9.2

Superb

29 reviews

$239
Average price / night
Check Availability
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator Pool and Lobby
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator Pool and Lobby
Apartment
Hancock, MA, USA
1.1k from Hancock center

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

1 Bedroom4 Guests
7.0

Good

1 reviews

$260
Average price / night
Check Availability
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
Condo
Hancock, MA, 01237, United States
1.4k from Hancock center

AC, Arcade, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

2 Bedrooms4 Guests
9.8

Exceptional

21 reviews

$257
Average price / night
Check Availability
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
House
Hancock, MA, USA
1.1k from Hancock center

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

2 Bedrooms7 Guests
1.0

Review score

1 reviews

$357
Average price / night
Check Availability
Newly renovated townhouse, sleeps 8 located at Jiminy Peak Ski Resort
Newly renovated townhouse, sleeps 8 located at Jiminy Peak Ski Resort
House
Hancock, MA, 01237, United States
1.6k from Hancock center

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

3 Bedrooms8 Guests
9.8

Exceptional

19 reviews

$383
Average price / night
Check Availability
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
1.1k from Hancock 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
Clean+Comfy1BRw/Views! OpenLR/D/K! GasFP, HPool,HTub, WorkRemote+Play AllYear!🤗
Clean+Comfy1BRw/Views! OpenLR/D/K! GasFP, HPool,HTub, WorkRemote+Play AllYear!🤗
Condo
Hancock, MA, 01237, United States
1.8k from Hancock center

AC, Arcade, Balcony, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$210
Average price / night
Check Availability
2 BR JIMINY PEAK w Mountain Views SLEEPS 7 Gorgeous
2 BR JIMINY PEAK w Mountain Views SLEEPS 7 Gorgeous
House
Hancock, MA, USA
1.1k from Hancock center

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

2 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$260
Average price / night
Check Availability
Vacation Village in the Berkshires
Vacation Village in the Berkshires
Condo
276 Brodie Mountain Rd, Williamstown, MA, 01237, United States
2.0k from Hancock center

AC, Arcade, Business Services, Fireplace, Fitness Equipment, Free Parking, Frontdesk 24 Hour, Heater, Internet

1 Bedroom4 Guests
8.8

Fabulous

2324 reviews

$165
Average price / night
Check Availability
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Apartment
Hancock, MA, USA
1.1k from Hancock center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay, Condos

1 Bedroom4 Guests
7.5

Good

2 reviews

$167
Average price / night
Check Availability
🌞Views! 2m2Ski! 1BR King Condo! OpenLR/DR/K! FP HPool,Jacuzzi, Gym+KidsStuff🌞!
🌞Views! 2m2Ski! 1BR King Condo! OpenLR/DR/K! FP HPool,Jacuzzi, Gym+KidsStuff🌞!
Condo
Hancock, MA, 01237, United States
2.0k from Hancock center

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

1 Bedroom4 Guests
4.0

Review score

1 reviews

$202
Average price / night
Check Availability
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
3.0k from Hancock center

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

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$499
Average price / night
Check Availability
Hancock Village Inn Near Jiminy Peak
Hancock Village Inn Near Jiminy Peak
House
Hancock, MA, 01237, United States
3.1k from Hancock center

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

6 Bedrooms17 Guests
10.0

Exceptional

19 reviews

$1148
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
3.2k from Hancock 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
Winterberry Lodge: NEWLY RENOVATED Spacious Berkshire Getaway at Jiminy Peak
Winterberry Lodge: NEWLY RENOVATED Spacious Berkshire Getaway at Jiminy Peak
Condo
Hancock, MA, 01237, United States
3.3k from Hancock center

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

3 Bedrooms10 Guests
New to Booking
$454
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 Hancock.

Stay Near Hancock's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Hancock Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 70 verified family-friendly vacation rentals in Hancock. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Hancock vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $165 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Hancock 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 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 often include amenities such as Fireplace/Heating, Child Friendly, 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.