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

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1488 Best 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
Check Availability
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
Check Availability
5 Bedrooms | Water Views | Private Pond Beach | Outdoor Shower
5 Bedrooms | Water Views | Private Pond Beach | Outdoor Shower
House
Brewster, MA, 02631, United States
0.8k from Brewster center

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

5 Bedrooms12 Guests
New to Booking
$599
Average price / night
Check Availability
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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Lovely home w/free WiFi/spacious patio/spiral staircase - near shops/restaurants
Lovely home w/free WiFi/spacious patio/spiral staircase - near shops/restaurants
House
Brewster, MA, 02631, United States
0.8k from Brewster center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Kitchen, Laundry

1 Bedroom6 Guests
8.8

Fabulous

21 reviews

$564
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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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
Check Availability
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
Check Availability
Private Oasis Near Rail Trail, Beaches, Dining (2425)
Private Oasis Near Rail Trail, Beaches, Dining (2425)
House
Brewster, MA, 02139, United States
1.0k from Brewster center

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

2 Bedrooms4 Guests
New to Booking
$413
Average price / night
Check Availability
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
Check Availability
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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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
Check Availability
Spectacular Coastal Living w salt water pool, close to beach & air conditioned
Spectacular Coastal Living w salt water pool, close to beach & air conditioned
House
Brewster, MA, 02631, United States
1.0k from Brewster center

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

6 Bedrooms12 Guests
10.0

Exceptional

25 reviews

$1994
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
Check Availability
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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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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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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Short walk to Sheep Pond Private Beach!
Short walk to Sheep Pond Private Beach!
House
Brewster, MA, 02631, United States
1.1k from Brewster center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$372
Average price / night
Check Availability
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
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
Check Availability
Enjoy Brewster With Years Of Family Charm
Enjoy Brewster With Years Of Family Charm
House
Brewster, MA, USA
1.8k from Brewster center

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

3 Bedrooms7 Guests
New to Booking
$593
Average price / night
Check Availability
Close to Bayside Beaches w/ Pool Table, Fire Pit
Close to Bayside Beaches w/ Pool Table, Fire Pit
House
Brewster, MA, 02631, United States
1.3k from Brewster center

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

4 Bedrooms9 Guests
9.8

Exceptional

11 reviews

$393
Average price / night
Check Availability
The Condo at Ocean Edge
The Condo at Ocean Edge
Apartment
Brewster, MA, USA
1.8k from Brewster center

Apartments, Accommodations, Lodgings, Places to stay, Condos

1 Bedroom4 Guests
7.3

Good

3 reviews

$408
Average price / night
Check Availability
Pond front with Private Beach and Central A/C
Pond front with Private Beach and Central A/C
House
Brewster, MA, 02631-2555, United States
1.4k from Brewster center

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

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$427
Average price / night
Check Availability
Old Cape Charmer
Old Cape Charmer
House
Brewster, MA, 02631, United States
1.4k from Brewster center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$613
Average price / night
Check Availability
House with Cottage in quaint Brewster, Central to Cape Attractions and Beaches
House with Cottage in quaint Brewster, Central to Cape Attractions and Beaches
House
Brewster, MA, 02631, United States
1.4k from Brewster center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Laundry, Microwave, No Smoking

4 Bedrooms12 Guests
New to Booking
$798
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 Vacation Rentals in Brewster.

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Frequently Asked Questions

You can explore 1488 verified vacation rentals in Brewster. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Brewster vary depending on the season, property size, and location. Rates typically start from around $265 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Brewster include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Brewster welcome pets. Currently, 51 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Brewster often include amenities such as Fireplace/Heating, Laundry, and Balcony/Terrace. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.