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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Winthrop Cottages

Our top choices for Winthrop cottages

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
Charming 1-bedroom seaside cottage in enchanting Marblehead with WiFi, AC
Outdoor spa tub

Charming 1-bedroom seaside cottage in enchanting Marblehead with WiFi, AC

Charming 1-bedroom seaside cottage in enchanting Marblehead with WiFi, AC
Cozy Pet Friendly House Next To Train
Exterior

Cozy Pet Friendly House Next To Train

2.0 star property
6.8 out of 10, (5)
"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
10.0 out of 10, Exceptional, (1)
The price is CA $498
CA $690 total
includes taxes & fees
Sep 8 - Sep 9
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
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!
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, (14)
"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
16 Mi to Boston: Home w/ Deck in Weymouth
House (3 Bedrooms) | Front of property

16 Mi to Boston: Home w/ Deck in Weymouth

3.0 star property
16 Mi to Boston: Home w/ Deck in Weymouth
Witchy Hideaway Cottage with AC, Outdoor Patio, Close to Salem & Downtown
Fridge, microwave, oven, stovetop

Witchy Hideaway Cottage with AC, Outdoor Patio, Close to Salem & Downtown

The price is CA $225
CA $462 total
includes taxes & fees
Aug 26 - Aug 27
Witchy Hideaway Cottage with AC, Outdoor Patio, Close to Salem & Downtown
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!
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
Bright & Pet-friendly Home: 2 Mi to Harvard Square
House (4 Bedrooms) | Private kitchen

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!
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!
Waterfront Views: Historic Marblehead Home
House (3 Bedrooms) | Interior

Waterfront Views: Historic Marblehead Home

3.0 star property
Waterfront Views: Historic Marblehead Home
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
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!
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 Winthrop Hotel Reviews

Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

10/10 Excellent
"Great location "
Mallory 1-night trip
Posted 8 hours ago
Copley Square Hotel, a FOUND Hotel