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

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600 Best Family Vacation Rentals in Brewster (Starting from $265)

Sheep Pond Bow House
Sheep Pond Bow House
House
Brewster, MA, USA
0.1k from Brewster center

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

4 Bedrooms8 Guests
New to Booking
$299
Average price / night
Check Availability
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
0.1k from Brewster 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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Relaxing Cape Getaway
Relaxing Cape Getaway
House
Brewster, MA, USA
0.8k from Brewster 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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Sheep’s Pond Retreat
Sheep’s Pond Retreat
Cottage
Brewster, MA, 02631, United States
1.0k from Brewster 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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Beautiful Home Close to Ponds and Beach
Beautiful Home Close to Ponds and Beach
House
Brewster, MA, USA
1.0k from Brewster 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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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
1.0k from Brewster 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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John Hazelnut
John Hazelnut
House
Brewster, Massachusetts, USA
1.0k from Brewster center

Air Conditioner, Parking, Balcony/Terrace, Kitchen, Laundry, Wheelchair Accessible, Internet

2 Bedrooms4 Guests
8.0

Good

1 reviews

$417
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
1.0k from Brewster 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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Close to Bayside Game Room w Pool Table
Close to Bayside Game Room w Pool Table
House
Brewster, MA, USA
1.3k from Brewster center

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

4 Bedrooms9 Guests
5.5

Review score

2 reviews

$499
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
1.1k from Brewster 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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Haven Cottage
Haven Cottage
House
Brewster, MA, USA
1.4k from Brewster center

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

4 Bedrooms10 Guests
8.0

Good

3 reviews

$281
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
1.3k from Brewster 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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Sand, Shells & Sunsets
Sand, Shells & Sunsets
Apartment
Brewster, MA, USA
1.6k from Brewster center

Apartments, Accommodations, Pools, Lodgings, Hot tubs, Places to stay

2 Bedrooms6 Guests
6.0

Review score

1 reviews

$475
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
1.3k from Brewster 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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Peaceful Retreat on Chilton Lane
Peaceful Retreat on Chilton Lane
House
Brewster, MA, USA
1.6k from Brewster center

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

2 Bedrooms5 Guests
New to Booking
$508
Average price / night
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Beautiful condo at Ocean Edge
Beautiful condo at Ocean Edge
Condo
Brewster, MA, 02631, United States
1.4k from Brewster 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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Ocean Mandevilla
Ocean Mandevilla
Apartment
Brewster, MA, USA
1.6k from Brewster center

Apartments, Accommodations, Pools, Lodgings, Vacation rentals, Hot tubs, Places to stay

2 Bedrooms6 Guests
8.2

Very Good

7 reviews

$453
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
1.5k from Brewster 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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The Blue Whale Cottage
The Blue Whale Cottage
House
Brewster, MA, USA
1.7k from Brewster center

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

3 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$387
Average price / night
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Peaceful Haven, Brewster Walk to The Brewster Store & Breakwater Beach
Peaceful Haven, Brewster Walk to The Brewster Store & Breakwater Beach
House
Brewster, MA, 02631, United States
1.6k from Brewster center

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

3 Bedrooms6 Guests
10.0

Exceptional

12 reviews

$557
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
1.8k from Brewster 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
Check Availability
Immaculately Clean - Continually  Updated – Ocean Edge
Immaculately Clean - Continually Updated – Ocean Edge
Condo
Brewster, MA, 02631, United States
1.6k from Brewster center

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

2 Bedrooms6 Guests
9.8

Exceptional

41 reviews

$341
Average price / night
Check Availability
Bright Brewster Beach House Short Walk to Beaches
Bright Brewster Beach House Short Walk to Beaches
House
Brewster, MA, 02631, United States
1.7k from Brewster center

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

3 Bedrooms8 Guests
New to Booking
$678
Average price / night
Check Availability
Cape Cod Playhouse: Deck, Hot Tub & Games
Cape Cod Playhouse: Deck, Hot Tub & Games
House
Brewster, MA, 02631, United States
1.7k from Brewster center

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

3 Bedrooms8 Guests
New to Booking
$520
Average price / night
Check Availability
Cozy Cape Condo minutes from Brewster Beaches
Cozy Cape Condo minutes from Brewster Beaches
Condo
Brewster, MA, 02631, United States
1.7k from Brewster center

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

2 Bedrooms8 Guests
8.0

Good

4 reviews

$522
Average price / night
Check Availability
Large Ocean Edge House - Sleeps 8. Pools, Pickleball & Golf
Large Ocean Edge House - Sleeps 8. Pools, Pickleball & Golf
House
Brewster, MA, 02631, United States
1.8k from Brewster center

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

3 Bedrooms8 Guests
9.4

Superb

3 reviews

$1092
Average price / night
Check Availability
Private Family-Friendly Home in Brewster with Expansive Backyard!
Private Family-Friendly Home in Brewster with Expansive Backyard!
House
Brewster, MA, 02631, United States
1.8k from Brewster center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$503
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 Brewster.

Stay Near Brewster's Top Attractions

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

Brewster Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 600 verified family-friendly vacation rentals in Brewster. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Brewster 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 Brewster 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 Brewster 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 Brewster often include amenities such as Child Friendly, Fireplace/Heating, and Laundry. 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.