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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Brookline and around

Charming 2 Bedroom, 2 Bath, Coastal Carriage House in Marblehead
Exterior

Charming 2 Bedroom, 2 Bath, Coastal Carriage House in Marblehead

Charming 2 Bedroom, 2 Bath, Coastal Carriage House in Marblehead
Cozy Pet Friendly House Next To Train
Exterior

Cozy Pet Friendly House Next To Train

2.0 star property
6.6 out of 10, (4)
"My family and I stayed here for 5 days in August and it was lovely! Thanks for everything. The beds were very comfortable and the house was very clean and nice."
Cozy Pet Friendly House Next To Train
Pet-friendly Home w/ Spacious Yard in Avon!
House (4 Bedrooms) | Interior

Pet-friendly Home w/ Spacious Yard in Avon!

3.0 star property
Pet-friendly Home w/ Spacious Yard in Avon!
Trail Access On-site: Gorgeous MCM Deck House!
House (4 Bedrooms) | Interior

Trail Access On-site: Gorgeous MCM Deck House!

3.0 star property
Trail Access On-site: Gorgeous MCM Deck House!
5 Mi to TD Garden: Quiet Medford Getaway!
House (2 Bedrooms) | Interior

5 Mi to TD Garden: Quiet Medford Getaway!

3.0 star property
5 Mi to TD Garden: Quiet Medford Getaway!
Bright & Pet-friendly Home: 2 Mi to Harvard Square
Exterior

Bright & Pet-friendly Home: 2 Mi to Harvard Square

3.0 star property
10.0 out of 10, Exceptional, (1)
Bright & Pet-friendly Home: 2 Mi to Harvard Square
Waterfront Retreat w/ Deck ~ 7 Mi to Boston!
Interior

Waterfront Retreat w/ Deck ~ 7 Mi to Boston!

3.0 star property
8.0 out of 10, Very good, (1)
"Comfortable place to stay on the water overlooking Boston Harbor and downtown. Sunsets are amazing behind the tall buildings of downtown. Trails close by for walking and sightseeing. Nice kitchen and bathrooms. We had trouble with getting any of the TV's to work and there was an annoying flood light shining on the back deck from the neighbors house all day and night. Other than those two things it was nice to have a house on the water with a fantastic view. "
Waterfront Retreat w/ Deck ~ 7 Mi to Boston!
The Beach Cottage at Sandy Cove: Serene Retreat
Exterior

The Beach Cottage at Sandy Cove: Serene Retreat

8.0 out of 10, Very good, (1)
"Great little place to stay for a family of 4! "
The Beach Cottage at Sandy Cove: Serene Retreat
Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub
House (3 Bedrooms) | Front of property

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

3.0 star property
Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub
Waterfront Views: Historic Marblehead Home
House (3 Bedrooms) | Interior

Waterfront Views: Historic Marblehead Home

3.0 star property
Waterfront Views: Historic Marblehead Home
Pet-friendly Revere Getaway, Steps From the T!
House (2 Bedrooms) | Interior

Pet-friendly Revere Getaway, Steps From the T!

3.0 star property
Pet-friendly Revere Getaway, Steps From the T!
Belmont Home < 3 Mi to Harvard Square!
Interior

Belmont Home < 3 Mi to Harvard Square!

3.0 star property
Belmont Home < 3 Mi to Harvard Square!
Bright and modern cottage, perfect space design with every detail you expect.
Property grounds

Bright and modern cottage, perfect space design with every detail you expect.

Bright and modern cottage, perfect space design with every detail you expect.
Great little cottage sitting behind the main house on 4 acres of property.
Property grounds

Great little cottage sitting behind the main house on 4 acres of property.

Great little cottage sitting behind the main house on 4 acres of property.
2 Mi to Gillette Stadium: Foxborough Retreat!
House (4 Bedrooms) | Interior

2 Mi to Gillette Stadium: Foxborough Retreat!

3.0 star property
2 Mi to Gillette Stadium: Foxborough Retreat!
Charming Boston Area Home < 1 Mi to Revere Beach!
Property grounds

Charming Boston Area Home < 1 Mi to Revere Beach!

3.0 star property
Charming Boston Area Home < 1 Mi to Revere Beach!
Charming Beach Cottage
Exterior

Charming Beach Cottage

10.0 out of 10, Exceptional, (1)
"Great location. Lovely island. Property has great view of the water from the enclosed patio. Everything inside is state of the art, from security to lighting and audio/video. Has everything you need and is not a hotel. We will come back."
Charming Beach Cottage
The Little House. Historic 2-BR waterfront cottage in Winchester w/ WiFi, AC
Property grounds

The Little House. Historic 2-BR waterfront cottage in Winchester w/ WiFi, AC

The Little House. Historic 2-BR waterfront cottage in Winchester w/ WiFi, AC
Entire near Boston Cottage House: MBTA, T, all major roads, parking
Exterior

Entire near Boston Cottage House: MBTA, T, all major roads, parking

Entire near Boston Cottage House: MBTA, T, all major roads, parking
16 Mi to Boston: Home w/ Deck in Weymouth
House (3 Bedrooms) | Interior

16 Mi to Boston: Home w/ Deck in Weymouth

3.0 star property
16 Mi to Boston: Home w/ Deck in Weymouth
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Brookline Hotel Reviews

Hilton Boston Logan Airport

Hilton Boston Logan Airport

10/10 Excellent
"Friendly staff, clean, close easy access to airport. Perfect for us. Nice little pub downstairs and cafe. "
Adriane 1-night trip
Posted 10 hours ago
Hilton Boston Logan Airport

Frequently asked questions

Why book your cottage in Brookline with Expedia?
Booking a cottage in Brookline is as simple as clicking on your travel dates and selecting your ideal place for outdoor recreation and relaxation. From chic retreats to inexpensive stays and cottages that offer amenities like a kitchenette, Expedia has something for all traveller tastes. As for unbeatable deals? We've got you covered!
How can I find cheap cottages in Brookline?
With Expedia's convenient filter tool, comparing cheap cottages in Brookline is easy. To find accommodation that are very pocket friendly, refine your search by star rating, budget and amenities.
What is there to do in Brookline near my cottage?
Brookline has enough sights and activities to keep you going for weeks, starting with Larz Anderson Auto Museum. John Fitzgerald Kennedy National Historic Site, Coolidge Corner Theatre and Larz Anderson Park are other impressive attractions. If you're hanging around a while, Frederick Law Olmsted National Historic Site and GASP are worthwhile additions to your itinerary.