Search Cottages in Winthrop

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Winthrop

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

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

Charming 2 Bedroom, 2 Bath, Coastal Carriage House in Marblehead
NEW -Lakefront 2 Bed / 3 bath + Extra Bed off of living room
Terrace/patio

NEW -Lakefront 2 Bed / 3 bath + Extra Bed off of living room

3.0 star property
10.0 out of 10, Exceptional, (10)
"We stayed at this lovely cottage on our trip to Salem,Ma and it is conveniently located within about 20 mins to Salem. While we were not visiting Salem we ventured around Gloucester and visited many delicious restaurants and viewed the ocean. 10/10 recommend and look forward to coming back!"
NEW -Lakefront 2 Bed / 3 bath + Extra Bed off of living room
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!
Summer Sea Cottage -On Scituate Harbor
Marina

Summer Sea Cottage -On Scituate Harbor

10.0 out of 10, Exceptional, (2)
"Thanks for the great hospitality!"
Summer Sea Cottage -On Scituate Harbor
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!
COZY, MODERN, Charming Cottage 1min to the beach
Terrace/patio

COZY, MODERN, Charming Cottage 1min to the beach

9.0 out of 10, Wonderful, (7)
"Very charming house in cool location. It was very easy to reach all of Boston's attractions by public transportation with a pleasant walk to the Red Line. This house was the perfect accommodation for our family."
COZY, MODERN, Charming Cottage 1min to the beach
Unique Scituate Vacation Rental on Herring River!
Interior

Unique Scituate Vacation Rental on Herring River!

3.0 star property
Unique Scituate Vacation Rental on Herring River!
Bright & Pet-friendly Home: 2 Mi to Harvard Square
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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!
House (1 Bedroom) | 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!
10 Mi to Crane Beach: Wooded Home Near Boston!
House (4 Bedrooms) | Interior

10 Mi to Crane Beach: Wooded Home Near Boston!

3.0 star property
10 Mi to Crane Beach: Wooded Home Near Boston!
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!
Charming Scituate Home w/ Deck - Walk to Beaches!
Interior

Charming Scituate Home w/ Deck - Walk to Beaches!

3.0 star property
Charming Scituate Home w/ Deck - Walk to Beaches!
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
Interior

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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winthrop Hotel Reviews

The Dagny Boston

The Dagny Boston

10/10 Excellent
"Great Location!"
Jim 1-night trip
Posted 15 hours ago
The Dagny Boston

Frequently asked questions

Why book your cottage in Winthrop with Expedia?
Expedia has some great cottages in Winthrop, so get ready for a memorable stay on nature's doorstep. If you have a budget in mind, select how much you want to spend and the preferred star rating of your property. Or, use our handy filters to search for cottages with a kitchen or a pool. We'll help you find the right place whatever your getaway looks like.
How can I find cheap cottages in Winthrop?
Expedia can help you easily track down cheap cottages in Winthrop. To book your special stay in a matter of clicks, try out our handy filter tool to tailor your search results by amenities, budget and star rating.