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Compare 25 Cottages in Winthrop with updated reviews, rates, and availability.

The Shore House, steps to the ocean meet crisp clean beach side retreat!

8.0 out of 10, Very Good, (2)
"The house was quite lovely. We were expecting 2 rooms with twin beds but there was just 1 room with twin beds. Downstairs space was great. We were surprised that there wasn’t an outdoor space to barbecue and have dinner for a group. Deck was small so great for coffee but not a meal at the end of the day. There were some beach towels and bath towels but we expected more towels. AC worked well. The 1 bathroom was small. It would have helped to at least have an outdoor shower. For the price of our...
The Shore House, steps to the ocean meet crisp clean beach side retreat!

Unique Scituate Vacation Rental on Herring River!

3.0 star property
Unique Scituate Vacation Rental on Herring River!

COZY, MODERN, Charming Cottage 1min to the beach

9.0 out of 10, Wonderful, (7)
"This little cottage has a perfect location on Wollaston Beach right behind Tony’s Clam Shop. Walking distance to the water as well as a playground for kiddos. Back yard is fairly nice but not fenced and had some glass and nails about, so keep shoes on the little ones! Though hosts were otherwise prepared with a pack and play and high chair, which our family appreciated juggling multiple babies for the family reunion. Kitchen was great to cook in and the back porch was lovely for morning coffee...
COZY, MODERN, Charming Cottage 1min to the beach

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!

Cozy Pet Friendly House Next To Train

2.0 star property
6.6 out of 10, (4)
"It was a sad trip as we were dropping our daughter off for college. So it was a blessing to have this central location to be easy to check into to, keep clean, and feel safe. We were spooked out at the basement it that’s cause we do not have basements where we live. We let the horror stories about basements get the better of us. But that lasted like 60 minutes. Haha. I would rent this again. "
Cozy Pet Friendly House Next To Train

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

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

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

Pet-friendly Marblehead Home Near Preston Beach!

3.0 star property
Pet-friendly Marblehead Home Near Preston Beach!

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

4 Bedroom Cape house - steps to the beach

Charming Boston Area Home < 1 Mi to Revere Beach!

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

Waldingfield - Pool House / Sleeps 2

10.0 out of 10, Exceptional, (1)
"This property is a gem! It made for a perfect weekend getaway with my fiance. The pool house is just right for 2 people and the grounds are simply lovely. Edwin was a great host, providing a tour and lots of info about the area. I would stay here again in a heartbeat!"
Waldingfield - Pool House / Sleeps 2

Home w/ Backyard ~ 2 Mi to Downtown Lexington!

3.0 star property
Home w/ Backyard ~ 2 Mi to Downtown Lexington!

Pet-friendly Revere Getaway, Steps From the T!

3.0 star property
Pet-friendly Revere Getaway, Steps From the T!

Luxe 4BR 3 Bath North End & Faneuil Hall

3.0 star property
Luxe 4BR 3 Bath North End & Faneuil Hall

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

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

Weymouth Waterfront Getaway w/ Hot Tub & Pool!

3.0 star property
Weymouth Waterfront Getaway w/ Hot Tub & Pool!

Coastal Lynn Escape w/ Fireplace: 3 Mi to Beaches

3.0 star property
Coastal Lynn Escape w/ Fireplace: 3 Mi to Beaches

Charming Scituate Home w/ Deck - Walk to Beaches!

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

Waltham Vacation Rental ~ 12 Mi to Downtown Boston

3.0 star property
Waltham Vacation Rental ~ 12 Mi to Downtown Boston
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

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

10.0 out of 10, Exceptional, (39)
"My sister and I did a trip where we split a day in Boston and a day in Salem. This was a perfect place to stay for both. Frank was a lovely host who was very responsive and gave us a lot of good suggestions. We especially really enjoyed getting to use the balcony. My sister and I both said we would love to stay here again! "
The price is AED 518
AED 1,120 total
includes taxes & fees
2 Dec - 3 Dec
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very Good, (493)
"We enjoyed our stay. It was walkable to Chinatown. Very accessible to subway station. We liked that our room was on the top floor. "
The price is AED 526
AED 1,055 total
includes taxes & fees
8 Dec - 9 Dec
Global Luxury Suites Downtown Boston

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (152)
"Everything good "
The price is AED 298
AED 701 total
includes taxes & fees
27 Dec - 28 Dec
Maverick Suites at 28 Fenway
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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