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

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  4.  Massachusetts

  5.  Brewster
  6.  Sheep Pond

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660 Best Family Vacation Rentals in Sheep Pond (Starting from $265)

Beautiful Home Close to Ponds and Beach
Beautiful Home Close to Ponds and Beach
House
Brewster, MA, USA
0.7k from Sheep Pond center

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

3 Bedrooms8 Guests
9.5

Superb

2 reviews

$525
Average price / night
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Long Pond Lux Estate. Pickleball, Private Dock, Private Beach Access
Long Pond Lux Estate. Pickleball, Private Dock, Private Beach Access
House
Brewster, MA, 02631, United States
0.5k from Sheep Pond center

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

6 Bedrooms16 Guests
10.0

Exceptional

34 reviews

$2681
Average price / night
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Steps to Freshwater Beach Kayaks Sauna
Steps to Freshwater Beach Kayaks Sauna
House
Brewster, MA, USA
1.1k from Sheep Pond center

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

5 Bedrooms11 Guests
New to Booking
$1109
Average price / night
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Sheep’s Pond Retreat
Sheep’s Pond Retreat
Cottage
Brewster, MA, 02631, United States
0.8k from Sheep Pond center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$283
Average price / night
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Sheep Pond Bow House
Sheep Pond Bow House
House
Brewster, MA, USA
1.1k from Sheep Pond center

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

4 Bedrooms8 Guests
New to Booking
$299
Average price / night
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Cozy family retreat with kayaks, board games, AC, and beach access
Cozy family retreat with kayaks, board games, AC, and beach access
House
Brewster, MA, 02631, United States
1.1k from Sheep Pond center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$861
Average price / night
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Lucky Landing
Lucky Landing
House
Brewster, MA, USA
1.5k from Sheep Pond center

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

4 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$500
Average price / night
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Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
House
Brewster, MA, 02631, United States
1.6k from Sheep Pond center

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

3 Bedrooms7 Guests
10.0

Exceptional

25 reviews

$714
Average price / night
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Hot Tub 1 Mile to Swimming on Long Pond
Hot Tub 1 Mile to Swimming on Long Pond
House
Brewster, MA, USA
1.6k from Sheep Pond center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$599
Average price / night
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Brewster 3 Bedroom getaway with plenty of green space!
Brewster 3 Bedroom getaway with plenty of green space!
House
Brewster, MA, 02631, United States
1.8k from Sheep Pond center

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

3 Bedrooms8 Guests
8.8

Fabulous

8 reviews

$354
Average price / night
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Cozy Charming Cottage
Cozy Charming Cottage
House
Brewster, MA, USA
1.7k from Sheep Pond center

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

3 Bedrooms9 Guests
9.3

Superb

4 reviews

$915
Average price / night
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Shop, Swim, Hike, Bike in Historic Brewster MA!
Shop, Swim, Hike, Bike in Historic Brewster MA!
House
Brewster, MA, 02613, United States
1.8k from Sheep Pond center

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

3 Bedrooms7 Guests
9.8

Exceptional

35 reviews

$266
Average price / night
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Spacious Home by Beach Dog Welcome
Spacious Home by Beach Dog Welcome
House
Brewster, MA, USA
1.8k from Sheep Pond center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$479
Average price / night
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Ocean Edge Luxury Condo,  Constantly Updated, Just steps to Arbor Pool
Ocean Edge Luxury Condo, Constantly Updated, Just steps to Arbor Pool
Condo
Brewster, MA, 02631, United States
1.9k from Sheep Pond center

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

3 Bedrooms6 Guests
10.0

Exceptional

127 reviews

$644
Average price / night
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Spacious Home with Private In-Ground Pool
Spacious Home with Private In-Ground Pool
House
Brewster, MA, USA
1.8k from Sheep Pond center

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

5 Bedrooms10 Guests
9.0

Fabulous

1 reviews

$1175
Average price / night
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VILLA at Ocean Edge Endicott Village, GOLF PRIVILEGES AND VIEW. LINENS PROVIDED
VILLA at Ocean Edge Endicott Village, GOLF PRIVILEGES AND VIEW. LINENS PROVIDED
Villa
Brewster,, MA, 02631, United States
1.9k from Sheep Pond center

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

3 Bedrooms8 Guests
9.8

Exceptional

81 reviews

$553
Average price / night
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Brewster Getaway
Brewster Getaway
House
Brewster, MA, USA
1.8k from Sheep Pond center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$538
Average price / night
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Private Lake Beach on Bike Path,  Air Conditioning, Outdoor Patio w/Fire Place.
Private Lake Beach on Bike Path, Air Conditioning, Outdoor Patio w/Fire Place.
House
Brewster, MA, 02631, United States
1.9k from Sheep Pond center

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

5 Bedrooms10 Guests
9.6

Exceptional

27 reviews

$784
Average price / night
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Relaxing Cape Getaway
Relaxing Cape Getaway
House
Brewster, MA, USA
1.8k from Sheep Pond center

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

1 Bedroom6 Guests
7.8

Good

6 reviews

$349
Average price / night
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Charming 3-bedroom condo in Endicott Village at Ocean Edge Resort & Golf Club
Charming 3-bedroom condo in Endicott Village at Ocean Edge Resort & Golf Club
Condo
Brewster, MA, 02631, United States
2.0k from Sheep Pond center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$715
Average price / night
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122 Tracy Lane Brewster Cape Cod - Jack's Little Cape House
122 Tracy Lane Brewster Cape Cod - Jack's Little Cape House
House
Brewster, MA, USA
1.8k from Sheep Pond center

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

1 Bedroom8 Guests
New to Booking
$360
Average price / night
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Escape to Brewster's charm, just a quick 6-min drive to Cape Cod Beaches
Escape to Brewster's charm, just a quick 6-min drive to Cape Cod Beaches
House
Brewster, MA, 02631, United States
2.0k from Sheep Pond center

Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.2

Superb

32 reviews

$265
Average price / night
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★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets
★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets
House
Harwich, MA, 02645, United States
2.0k from Sheep Pond center

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

3 Bedrooms6 Guests
10.0

Exceptional

25 reviews

$541
Average price / night
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Private Family-Friendly Home in Brewster with Expansive Backyard!
Private Family-Friendly Home in Brewster with Expansive Backyard!
House
Brewster, MA, 02631, United States
2.0k from Sheep Pond center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$503
Average price / night
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Cape Cod Playhouse: Deck, Hot Tub & Games
Cape Cod Playhouse: Deck, Hot Tub & Games
House
Brewster, MA, 02631, United States
2.1k from Sheep Pond center

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

3 Bedrooms8 Guests
New to Booking
$520
Average price / night
Check Availability
Beautiful condo at Ocean Edge
Beautiful condo at Ocean Edge
Condo
Brewster, MA, 02631, United States
2.1k from Sheep Pond center

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

2 Bedrooms6 Guests
9.0

Fabulous

9 reviews

$373
Average price / night
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Modern Cape, Private Heated Salt Water Pool,  Minutes to Beaches/Golf/Lakes
Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf/Lakes
House
Brewster, MA, 02631, United States
2.2k from Sheep Pond center

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

4 Bedrooms12 Guests
10.0

Exceptional

30 reviews

$785
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 Sheep Pond.

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Sheep Pond Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 660 verified family-friendly vacation rentals in Sheep Pond. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Sheep Pond vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $265 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Sheep Pond 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 Sheep Pond 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 Sheep Pond 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.