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

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  2. Family Vacation Rentals
  3.  USA

  4.  Massachusetts

  5.  Becket
  6.  Sherwood Forest

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28 Best Family Vacation Rentals in Sherwood Forest (Starting from $152)

Becket Home with 3-Season Porch Walk to Lake Access
Becket Home with 3-Season Porch Walk to Lake Access
House
Becket, MA, USA
0.3k from Sherwood Forest center

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

2 Bedrooms7 Guests
8.0

Good

1 reviews

$294
Average price / night
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Lakefront Jewel By: Evergreen Home
Lakefront Jewel By: Evergreen Home
House
Becket, MA, 01223, United States
0.2k from Sherwood Forest center

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

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$464
Average price / night
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A-Frame Cabin with Furnished Deck in Becket!
A-Frame Cabin with Furnished Deck in Becket!
House
Becket, MA, USA
2.2k from Sherwood Forest center

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

2 Bedrooms6 Guests
6.5

Good

2 reviews

$165
Average price / night
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Berkshires Lakefront Retreat\n
Berkshires Lakefront Retreat\n
House
Becket, MA, 01223, United States
0.7k from Sherwood Forest center

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

3 Bedrooms10 Guests
10.0

Exceptional

19 reviews

$524
Average price / night
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Berkshires Home on 11 Acres with Pond and 2 Fire Pits!
Berkshires Home on 11 Acres with Pond and 2 Fire Pits!
House
Becket, MA, USA
3.4k from Sherwood Forest center

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

3 Bedrooms8 Guests
New to Booking
$405
Average price / night
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Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
House
Becket, MA, 01223, United States
0.9k from Sherwood Forest center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

5 reviews

$375
Average price / night
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Berkshires Cabin 2 Mi to Appalachian Trail!
Berkshires Cabin 2 Mi to Appalachian Trail!
House
Otis, MA, USA
6.3k from Sherwood Forest center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

3 Bedrooms7 Guests
9.0

Fabulous

1 reviews

$576
Average price / night
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Serene, Private Waterfront House --Perfect Summer Retreat!
Serene, Private Waterfront House --Perfect Summer Retreat!
House
Becket, MA, 01223, United States
0.9k from Sherwood Forest center

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

3 Bedrooms6 Guests
9.8

Exceptional

129 reviews

$290
Average price / night
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Cozy Berkshires Vacation Rental Near Hiking!
Cozy Berkshires Vacation Rental Near Hiking!
Apartment
Chester, MA, USA
7.6k from Sherwood Forest center

Guest Services, Parking, Accessibility, Security/Safety, Internet, Sports/Activities, Pet Friendly

2 Bedrooms6 Guests
New to Booking
$152
Average price / night
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Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
House
Becket, MA, 01223, United States
1.0k from Sherwood Forest center

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

2 Bedrooms7 Guests
9.8

Exceptional

14 reviews

$393
Average price / night
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Starry Skies, Sauna & Smores Your Fall Getaway
Starry Skies, Sauna & Smores Your Fall Getaway
Ski Chalet
Otis, MA, USA
7.7k from Sherwood Forest center

Cheap, Accommodations, Parking, Cabins, Cottages, Lodgings, Vacation rentals, Places to stay, Family

17 Bedrooms10 Guests
9.3

Superb

3 reviews

$533
Average price / night
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Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!
Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!
House
Becket, MA, 01223, United States
2.0k from Sherwood Forest center

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

4 Bedrooms8 Guests
10.0

Exceptional

99 reviews

$351
Average price / night
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Lakefront Otis Home with Stunning Views and Boats!
Lakefront Otis Home with Stunning Views and Boats!
House
Otis, MA, USA
8.7k from Sherwood Forest center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$346
Average price / night
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Little Longbow Lakefront Chalet
Little Longbow Lakefront Chalet
Ski Chalet
Becket, MA, 01223, United States
2.2k from Sherwood Forest center

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

2 Bedrooms5 Guests
9.8

Exceptional

23 reviews

$430
Average price / night
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Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
House
Becket, MA, 01223, United States
3.6k from Sherwood Forest center

Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

38 reviews

$578
Average price / night
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Lake, Tennis, Beach Access, Skiing, Kayaking, Fishing
Lake, Tennis, Beach Access, Skiing, Kayaking, Fishing
House
Otis, MA, 01029, United States
4.5k from Sherwood Forest center

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

3 Bedrooms6 Guests
New to Booking
$209
Average price / night
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Berkshire Lake at the Pillow, and EV!
Berkshire Lake at the Pillow, and EV!
House
Otis, MA, 01253, United States
5.5k from Sherwood Forest center

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

4 Bedrooms8 Guests
9.6

Exceptional

18 reviews

$384
Average price / night
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Serene Berkshires Cabin w/ Deck & Fire Pit!
Serene Berkshires Cabin w/ Deck & Fire Pit!
House
Otis, MA, 01253, United States
6.0k from Sherwood Forest center

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

4 Bedrooms8 Guests
New to Booking
$619
Average price / night
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Chalet in the Berkshires, Wellness, Ski, Sauna, Gas Fireplace EV charger & Home Office
Chalet in the Berkshires, Wellness, Ski, Sauna, Gas Fireplace EV charger & Home Office
Ski Chalet
Otis, MA, 01029, United States
7.4k from Sherwood Forest center

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

5 Bedrooms10 Guests
10.0

Exceptional

9 reviews

$714
Average price / night
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The Owl and Firefly – A Cabin for Families
The Owl and Firefly – A Cabin for Families
House
Otis, MA, 01253, United States
7.5k from Sherwood Forest center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Heater, Internet, Kitchen

3 Bedrooms10 Guests
New to Booking
$402
Average price / night
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Quintessential 1860's Berkshire farmhouse with mountain views on 30 acres.
Quintessential 1860's Berkshire farmhouse with mountain views on 30 acres.
House
Becket, MA, 01223, United States
7.6k from Sherwood Forest center

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

4 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$426
Average price / night
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Berkshire Holiday Home with Hot Tub & A+ Amenities
Berkshire Holiday Home with Hot Tub & A+ Amenities
House
Otis, MA, 01253, United States
8.2k from Sherwood Forest center

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

4 Bedrooms6 Guests
New to Booking
$355
Average price / night
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Tranquil 3-bedroom house with AC in charming Berkshires
Tranquil 3-bedroom house with AC in charming Berkshires
House
Otis, MA, 01253, United States
8.8k from Sherwood Forest center

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

3 Bedrooms8 Guests
New to Booking
$431
Average price / night
Check Availability
Custom Home on 9 scenic acres near small lake, Sleeps up to 16.
Custom Home on 9 scenic acres near small lake, Sleeps up to 16.
House
Otis, MA, 01253, United States
8.8k from Sherwood Forest center

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

4 Bedrooms16 Guests
10.0

Exceptional

119 reviews

$671
Average price / night
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4Br/3bath Lakefront/Ski House in Berkshires.  Hi speed wifi
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
House
East Otis, MA, 01029, United States
9.9k from Sherwood Forest center

Arcade, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

166 reviews

$290
Average price / night
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Modern Berkshires Cottage  🌲 Gas Stove, Large Deck & W/D + 7 mins to Otis Ridge
Modern Berkshires Cottage 🌲 Gas Stove, Large Deck & W/D + 7 mins to Otis Ridge
House
East Otis, MA, 01029, United States
9.9k from Sherwood Forest center

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

2 Bedrooms8 Guests
10.0

Exceptional

62 reviews

$285
Average price / night
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Private Island - Largest Fresh Water Reservoir in Mass
Private Island - Largest Fresh Water Reservoir in Mass
Cottage
Otis, MA, 01253, United States
10.0k from Sherwood Forest center

AC, Barbecue, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Living Area

2 Bedrooms6 Guests
8.6

Fabulous

9 reviews

$501
Average price / night
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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 Sherwood Forest.

Sherwood Forest Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 28 verified family-friendly vacation rentals in Sherwood Forest. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Sherwood Forest vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $152 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Sherwood Forest 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 Sherwood Forest 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 Sherwood Forest often include amenities such as Child Friendly, Fireplace/Heating, and Wellness Facilities. 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.