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

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33 Best Family Vacation Rentals in Sheffield (Starting from $217)

Water-View Home in the Berkshires
Water-View Home in the Berkshires
House
Sheffield, MA, USA
3.4k from Sheffield center

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

3 Bedrooms6 Guests
9.0

Fabulous

3 reviews

$534
Average price / night
Check Availability
Berkshires Walk to Brewery or Distillery with Peloton!
Berkshires Walk to Brewery or Distillery with Peloton!
House
Sheffield, MA, 01257, United States
1.2k from Sheffield center

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

3 Bedrooms5 Guests
9.8

Exceptional

8 reviews

$405
Average price / night
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Whitney by AvantStay Private Berkshires Estate
Whitney by AvantStay Private Berkshires Estate
House
Sheffield, MA, USA
4.0k from Sheffield center

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

1 Bedroom10 Guests
New to Booking
$217
Average price / night
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12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room
12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room
House
Sheffield, MA, 01257, United States
2.7k from Sheffield center

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

4 Bedrooms12 Guests
10.0

Exceptional

31 reviews

$511
Average price / night
Check Availability
Summer and Fall in Sheffield with Monthly Special Pricing Available
Summer and Fall in Sheffield with Monthly Special Pricing Available
House
Sheffield, MA, USA
4.6k from Sheffield center

Barbecue/Outdoor Cooking, Security/Safety, Sports/Activities, Pool, Pet Friendly, Internet, Skiing

6 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$299
Average price / night
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Gorgeous Sheffield Home in Heart of Berkshires
Gorgeous Sheffield Home in Heart of Berkshires
House
Sheffield, MA, 01257, United States
3.3k from Sheffield center

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

5 Bedrooms15 Guests
10.0

Exceptional

52 reviews

$697
Average price / night
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Ashley Falls Home with Fire Pit Hike and Ski!
Ashley Falls Home with Fire Pit Hike and Ski!
House
MA, USA
6.0k from Sheffield center

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

5 Bedrooms10 Guests
9.0

Fabulous

1 reviews

$231
Average price / night
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Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly
Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly
House
Sheffield, MA, 01257, United States
3.4k from Sheffield center

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

4 Bedrooms9 Guests
10.0

Exceptional

120 reviews

$989
Average price / night
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4 Mi to Great Barrington Berkshires Retreat!
4 Mi to Great Barrington Berkshires Retreat!
House
Sheffield, MA, USA
6.2k from Sheffield center

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

3 Bedrooms8 Guests
New to Booking
$326
Average price / night
Check Availability
Historic (updated)1812 Federal brick house well situated in Berkshires with pool
Historic (updated)1812 Federal brick house well situated in Berkshires with pool
House
Sheffield, MA, 01257, United States
3.7k from Sheffield center

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

4 Bedrooms8 Guests
8.0

Good

1 reviews

$1391
Average price / night
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Near Hiking Renovated 4-Acre Berkshires Retreat!
Near Hiking Renovated 4-Acre Berkshires Retreat!
House
South Egremont, MA, USA
8.0k from Sheffield center

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

3 Bedrooms8 Guests
New to Booking
$713
Average price / night
Check Availability
Luxury Private Estate in the Berkshires | Whitney by AvantStay
Luxury Private Estate in the Berkshires | Whitney by AvantStay
House
Sheffield, MA, 01257, United States
4.2k from Sheffield center

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

5 Bedrooms10 Guests
8.6

Fabulous

15 reviews

$465
Average price / night
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The Mill River Cabin with Fireplace and River View!
The Mill River Cabin with Fireplace and River View!
House
Mill River, MA, USA
8.3k from Sheffield center

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

2 Bedrooms5 Guests
10.0

Exceptional

6 reviews

$259
Average price / night
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52-Acre Farmhouse • Fire Pit + Outdoor Dining & Trails | Copper Kettle Farm
52-Acre Farmhouse • Fire Pit + Outdoor Dining & Trails | Copper Kettle Farm
House
Sheffield, MA, 01257, United States
4.4k from Sheffield center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area

4 Bedrooms14 Guests
New to Booking
$786
Average price / night
Check Availability
Guesthouse Cabin vacation rentals in Berkshire County
Guesthouse Cabin vacation rentals in Berkshire County
Cabin
Sheffield, MA, 01257, United States
5.7k from Sheffield center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

4 Bedrooms12 Guests
10.0

Exceptional

10 reviews

$683
Average price / night
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Antique Farmhouse Totally Restored
Antique Farmhouse Totally Restored
House
Sheffield, MA, 01257, United States
5.9k from Sheffield center

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

4 Bedrooms16 Guests
9.8

Exceptional

97 reviews

$595
Average price / night
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Luxurious Mountain Retreat - Private 40-Acre Family Haven
Luxurious Mountain Retreat - Private 40-Acre Family Haven
House
Sheffield, MA, 01257, United States
6.9k from Sheffield center

AC, Babysitting, Barbecue, Breakfast Available, Crib, Dryer, Fitness Equipment, Free Parking, Heater

4 Bedrooms9 Guests
9.6

Exceptional

9 reviews

$843
Average price / night
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Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington
Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington
House
Sheffield, MA, 01222, United States
7.0k from Sheffield center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$487
Average price / night
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Restful pastoral, kids-friendly house w/ gardens, views, swimming pool, sauna
Restful pastoral, kids-friendly house w/ gardens, views, swimming pool, sauna
House
Southfield, MA, 01259, United States
7.0k from Sheffield center

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

4 Bedrooms8 Guests
10.0

Exceptional

21 reviews

$463
Average price / night
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 Konkapot Cottage, Pastoral Bliss With Wide Views
Konkapot Cottage, Pastoral Bliss With Wide Views
House
New Marlborough, MA, 01259, United States
7.1k from Sheffield center

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

3 Bedrooms6 Guests
10.0

Exceptional

21 reviews

$331
Average price / night
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Cozy Log Cabin Retreat with Pool on 4 Acres
Cozy Log Cabin Retreat with Pool on 4 Acres
House
North Canaan, CT, 06018, United States
7.3k from Sheffield center

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

3 Bedrooms7 Guests
9.6

Exceptional

8 reviews

$396
Average price / night
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Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views
Cottage
Salisbury, CT, 06068, United States
7.7k from Sheffield center

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

2 Bedrooms6 Guests
9.6

Exceptional

212 reviews

$277
Average price / night
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Lux Berkshire Mountain Haven: New reno, private road/acreage, best locale & ski!
Lux Berkshire Mountain Haven: New reno, private road/acreage, best locale & ski!
House
Egremont, MA, 01230, United States
8.0k from Sheffield center

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

3 Bedrooms8 Guests
New to Booking
$765
Average price / night
Check Availability
Fall/Winter Mountain Spa Nature Retreat with 15 Acre Trail System
Fall/Winter Mountain Spa Nature Retreat with 15 Acre Trail System
Apartment
Mt Washington, MA, 01258, United States
8.2k from Sheffield center

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

3 Bedrooms6 Guests
9.6

Exceptional

24 reviews

$302
Average price / night
Check Availability
Winter Ski Chalet w/ Cozy Fireplace + Private Hiking Trails
Winter Ski Chalet w/ Cozy Fireplace + Private Hiking Trails
House
Great Barrington, MA, 01230, United States
8.6k from Sheffield center

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

4 Bedrooms8 Guests
9.6

Exceptional

12 reviews

$868
Average price / night
Check Availability
Converted Berkshire schoolhouse on a quiet river
Converted Berkshire schoolhouse on a quiet river
House
New Marlborough, MA, 01259, United States
8.7k from Sheffield center

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

3 Bedrooms5 Guests
10.0

Exceptional

39 reviews

$289
Average price / night
Check Availability
Country Castle-Total privacy-just a few minutes from center of Great Barrington
Country Castle-Total privacy-just a few minutes from center of Great Barrington
House
Great Barrington, MA, 01230, United States
8.8k from Sheffield center

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

6 Bedrooms13 Guests
10.0

Exceptional

2 reviews

$1274
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 Sheffield.

Stay Near Sheffield's Top Attractions

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

Sheffield Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 33 verified family-friendly vacation rentals in Sheffield. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Sheffield vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $217 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Sheffield 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 Sheffield 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 Sheffield 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.