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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

Compare 24 Cottages in Winthrop with updated reviews, rates, and availability.

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
Quiet and Cozy Cottage at Sandy Cove 1 BR Sleeps 4
Fridge, microwave, oven, stovetop

Quiet and Cozy Cottage at Sandy Cove 1 BR Sleeps 4

10.0 out of 10, Exceptional, (1)
"Perfect getaway cottage in great location in Cohasset. Great communication with the owner."
Quiet and Cozy Cottage at Sandy Cove 1 BR Sleeps 4
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!
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
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!
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 Views: Historic Marblehead Home
Interior

Waterfront Views: Historic Marblehead Home

3.0 star property
Waterfront Views: Historic Marblehead Home
NEW -Lakefront 2 Bed / 3 bath + Extra Bed off of living room
Interior

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

3.0 star property
10.0 out of 10, Exceptional, (8)
"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
The Little House. Historic 2-BR waterfront cottage in Winchester w/ WiFi, AC
Terrace/patio

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
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
4 Bedroom Cape house - steps to the beach
Terrace/patio

4 Bedroom Cape house - steps to the beach

4 Bedroom Cape house - steps to the beach
Entire near Boston Cottage House: MBTA, T, all major roads, parking
Terrace/patio

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

Entire near Boston Cottage House: MBTA, T, all major roads, parking
Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub
Interior

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

3.0 star property
Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub
Luxe 4BR 3 Bath North End & Faneuil Hall
House (4 Bedrooms) | Private kitchen | Oven, stovetop, dishwasher, espresso maker

Luxe 4BR 3 Bath North End & Faneuil Hall

3.0 star property
Luxe 4BR 3 Bath North End & Faneuil Hall
Waltham Vacation Rental ~ 12 Mi to Downtown Boston
Interior

Waltham Vacation Rental ~ 12 Mi to Downtown Boston

3.0 star property
Waltham Vacation Rental ~ 12 Mi to Downtown Boston
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!
Pet-friendly Revere Getaway, Steps From the T!
Microwave, oven, stovetop, dishwasher

Pet-friendly Revere Getaway, Steps From the T!

3.0 star property
Pet-friendly Revere Getaway, Steps From the T!
Pet-friendly Lynn Home w/ Patio - 3 Mi to Beach!
Microwave, oven, stovetop, dishwasher

Pet-friendly Lynn Home w/ Patio - 3 Mi to Beach!

3.0 star property
Pet-friendly Lynn Home w/ Patio - 3 Mi to Beach!
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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Other property types in Winthrop

Sonder 907 Main
Interior

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (470)
"The location was great. Close to the metro and good dining options. "
The price is SAR 583
SAR 676 total
includes taxes & fees
26 May - 27 May
Sonder 907 Main
Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | Living area | 50-inch Smart TV with satellite channels, Netflix, Hulu

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (192)
"Amazing stay, thank you!"
The price is SAR 446
SAR 879 total
includes taxes & fees
5 May - 6 May
Maverick Suites at 28 Fenway
Temple Place Suites
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

2.5 star property
6.8 out of 10, (199)
"We loved how walkable this location was! It was easy to walk or find public transport for anywhere we needed! "
The price is SAR 446
SAR 719 total
includes taxes & fees
4 May - 5 May
Temple Place Suites
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.