Brewster, Massachusetts

Vacation Rentals in Brewster, Massachusetts

Discover 271 vacation rental properties in Brewster. From 1 to 10 bedrooms. Average $405/night. 100% have pools.

271 verified listings Book securely on VRBO Prices updated March 2026

271 properties available

Authentic Cape Cod Saltbox - Antique home with modern conveniences

Authentic Cape Cod Saltbox - Antique home with modern conveniences

2 beds 2 baths
PoolA/CWiFiBalcony
$170/night
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Updated Brewster Cottage

Updated Brewster Cottage

2 beds 1 bath
PoolA/CWiFiBalcony
$222/night
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Central A/C Mins. to Beach Dog Welcome!

Central A/C Mins. to Beach Dog Welcome!

3 beds 2 baths
PoolA/CWiFiBalcony
$334/night
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Sunny Days Ahead! .6 Mile to Breakwater Beach

Sunny Days Ahead! .6 Mile to Breakwater Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$173/night
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Cozy Cape Cottage

Cozy Cape Cottage

1 bed 1 bath
PoolA/CWiFiBalcony
$253/night
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Secluded ranch home with a full outdoor shower & private community beach

Secluded ranch home with a full outdoor shower & private community beach

3 beds 2 baths
PoolA/CWiFiBalcony
$202/night
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Classic Cape: Huge Yard, Walk to Beaches, Brewster Flats, Restaurants & Bars

Classic Cape: Huge Yard, Walk to Beaches, Brewster Flats, Restaurants & Bars

4 beds 3 baths
PoolA/CWiFiBalcony
$569/night
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Stylish and Modern Upper Level End Unit Condo at OCEAN EDGE

Stylish and Modern Upper Level End Unit Condo at OCEAN EDGE

2 beds 2 baths
PoolA/CWiFiBalcony
$272/night
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Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

2 beds 2 baths
PoolA/CWiFiBalcony
$748/night
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Modern A-Frame cottage with Pool set on a Horse Farm. 5 minutes from the beach!

Modern A-Frame cottage with Pool set on a Horse Farm. 5 minutes from the beach!

2 beds 1 bath
PoolA/CWiFiBalcony
$605/night
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Huge Deck Outdoor Shower Dog Friendly!

Huge Deck Outdoor Shower Dog Friendly!

4 beds 1 bath
PoolA/CWiFiBalcony
$235/night
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Spacious Home by Beach Dog Welcome!

Spacious Home by Beach Dog Welcome!

3 beds 2 baths
PoolA/CWiFiBalcony
$202/night
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Large Ocean Edge House - Sleeps 8. Pools, Pickleball & Golf

Large Ocean Edge House - Sleeps 8. Pools, Pickleball & Golf

3 beds 2 baths
PoolA/CWiFiBalcony
$512/night
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Family Friendly Home on Cobbs Pond and 100 yards from Cape Cod Bay in Brewster!

Family Friendly Home on Cobbs Pond and 100 yards from Cape Cod Bay in Brewster!

4 beds 3 baths
PoolA/CWiFiBalcony
$358/night
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Quiet place to relax.

Quiet place to relax.

1 bed 1 bath
PoolA/CWiFiBalcony
$199/night
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Close to Bayside Beaches w/ Pool Table, Fire Pit

Close to Bayside Beaches w/ Pool Table, Fire Pit

4 beds 2 baths
PoolA/CWiFiBalcony
$225/night
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Shining Sea Condo

Shining Sea Condo

2 beds 2 baths
PoolA/CWiFiBalcony
$452/night
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Spacious, renovated townhouse beautifully decorated with nautical décor with a straight staircase.

Spacious, renovated townhouse beautifully decorated with nautical décor with a straight staircase.

2 beds 2 baths
PoolA/CWiFiBalcony
$244/night
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Updated Howland Village end unit

Updated Howland Village end unit

2 beds 2 baths
PoolA/CWiFiBalcony
$218/night
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Newly updated, traditional townhouse with recently renovated bathrooms - a favorite for our guests.

Newly updated, traditional townhouse with recently renovated bathrooms - a favorite for our guests.

2 beds 1 bath
PoolA/CWiFiBalcony
$202/night
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Less Than 1 Mile to Point of Rocks Beach

Less Than 1 Mile to Point of Rocks Beach

3 beds 1 bath
PoolA/CWiFiBalcony
$210/night
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Walk to Beach Dog Welcome!

Walk to Beach Dog Welcome!

3 beds 1 bath
PoolA/CWiFiBalcony
$182/night
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Wonderful Ocean Edge Apartment. Short drive to beaches, you will love the Brewster Flats!

Wonderful Ocean Edge Apartment. Short drive to beaches, you will love the Brewster Flats!

2 beds 2 baths
PoolA/CWiFiBalcony
$202/night
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Newly Remodel. Ocean Edge Resort. A/C all rooms. 1 King, 1 Queen & 2 Twin

Newly Remodel. Ocean Edge Resort. A/C all rooms. 1 King, 1 Queen & 2 Twin

3 beds 2 baths
PoolA/CWiFiBalcony
$338/night
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VILLA at Endicott Village GOLF PRIVILEGES AND VIEW Ocean Edge.LINENS PROVIDED

VILLA at Endicott Village GOLF PRIVILEGES AND VIEW Ocean Edge.LINENS PROVIDED

3 beds 2 baths
PoolA/CWiFiBalcony
$409/night
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Shop, Swim, Hike, Bike in Historic Brewster MA!

Shop, Swim, Hike, Bike in Historic Brewster MA!

3 beds 2 baths
PoolA/CWiFiBalcony
$427/night
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Newly Updated 5BR/2BA 2500Sqft Very Private Family Home, WiFi & Air Conditioned!

Newly Updated 5BR/2BA 2500Sqft Very Private Family Home, WiFi & Air Conditioned!

5 beds 2 baths
PoolA/CWiFiBalcony
$439/night
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Updated and Spacious, Walk to the Bay Cape. WiFi, Cntrl A/C, Yard...

Updated and Spacious, Walk to the Bay Cape. WiFi, Cntrl A/C, Yard...

3 beds 2 baths
PoolA/CWiFiBalcony
$305/night
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Just steps away from the tranquil shores of Cape Cod Bay. Enjoy Brewster at this cozy and well-maintained residence.

Just steps away from the tranquil shores of Cape Cod Bay. Enjoy Brewster at this cozy and well-maintained residence.

3 beds 1 bath
PoolA/CWiFiBalcony
$248/night
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New construction within 1 mile of bay beach and Nickerson Park

New construction within 1 mile of bay beach and Nickerson Park

2 beds 1 bath
PoolA/CWiFiBalcony
$301/night
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Ocean Edge Cape House with Beach, Pool, and AC ☀️ 🏖

Ocean Edge Cape House with Beach, Pool, and AC ☀️ 🏖

3 beds 2 baths
PoolA/CWiFiBalcony
$437/night
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PET FRIENDLY! Right on Nickerson, with Cape Cod bike trail behind house!

PET FRIENDLY! Right on Nickerson, with Cape Cod bike trail behind house!

3 beds 2 baths
PoolA/CWiFiBalcony
$166/night
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Wow! Private Pool, Game Room, and Fire Pit!

Wow! Private Pool, Game Room, and Fire Pit!

4 beds 2 baths
PoolA/CWiFiBalcony
$451/night
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Beautifully Furnished and Decorated Upper-Level Eaton Condo in Ocean Edge on Cape Cod!

Beautifully Furnished and Decorated Upper-Level Eaton Condo in Ocean Edge on Cape Cod!

2 beds 2 baths
PoolA/CWiFiBalcony
$222/night
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Stunning Home with Wet Bar Dog Welcome!

Stunning Home with Wet Bar Dog Welcome!

4 beds 2 baths
PoolA/CWiFiBalcony
$310/night
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HISTORIC LUXURY! Patio-firepit-2KingSuites

HISTORIC LUXURY! Patio-firepit-2KingSuites

3 beds 3 baths
PoolA/CWiFiBalcony
$425/night
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In-Ground Plunge Pool Dog Friendly!

In-Ground Plunge Pool Dog Friendly!

3 beds 2 baths
PoolA/CWiFiBalcony
$702/night
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Cape Cod Bay & Quivett Creek Views-Great Sunsets!

Cape Cod Bay & Quivett Creek Views-Great Sunsets!

3 beds 2 baths
PoolA/CWiFiBalcony
$417/night
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Cozy recently renovated cottage on private 2+ acers of wooded paradise.

Cozy recently renovated cottage on private 2+ acers of wooded paradise.

2 beds 1 bath
PoolA/CWiFiBalcony
$357/night
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Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

3 beds 2 baths
PoolA/CWiFiBalcony
$241/night
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Walk to Beach from Sea Salt Cottage

Walk to Beach from Sea Salt Cottage

4 beds 3 baths
PoolA/CWiFiBalcony
$566/night
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Walk to Beach, AC, WiFi, walk to bike path

Walk to Beach, AC, WiFi, walk to bike path

3 beds 2 baths
PoolA/CWiFiBalcony
$240/night
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Brewster's Favorite Beach, Paine's Creek on Cape Cod Bay, 6/10's of a mile

Brewster's Favorite Beach, Paine's Creek on Cape Cod Bay, 6/10's of a mile

4 beds 2 baths
PoolA/CWiFiBalcony
$423/night
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Delightful Bay Views

Delightful Bay Views

3 beds 2 baths
PoolA/CWiFiBalcony
$456/night
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Freshly Renovated for the Summer 2019!

Freshly Renovated for the Summer 2019!

3 beds 2 baths
PoolA/CWiFiBalcony
$358/night
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Cape Cod Cottage w/ Outdoor Shower: Walk to Beach!

Cape Cod Cottage w/ Outdoor Shower: Walk to Beach!

2 beds 2 baths
PoolA/CWiFiBalcony
$196/night
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Sunlit getaway with chef’s kitchen, kayaks & private beach access

Sunlit getaway with chef’s kitchen, kayaks & private beach access

3 beds 2 baths
PoolA/CWiFiBalcony
$296/night
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This wonderful Billington features 2 bedrooms and an open loft, as well as a remodeled kitchen.

This wonderful Billington features 2 bedrooms and an open loft, as well as a remodeled kitchen.

2 beds 2 baths
PoolA/CWiFiBalcony
$178/night
View Details → Book on VRBO

Showing 48 of 271 properties

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