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Search results; Over 1,000 homes in Winthrop

Top guest favorite
Apartment in Winthrop
Heated saltwater pool, steps from the beach
1 bedroom, 4 beds, 1 private bath
Aug 21 – 26
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4.97 out of 5 average rating, 344 reviews
Apartment in Winthrop
Panoramic ocean views with a deck
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 28 – Sep 2
Top guest favorite
Apartment in Winthrop
Oceanfront with direct beach access
4.98 out of 5 average rating, 52 reviews, 1 bedroom, 2 beds, 1 bath
Aug 20 – 25
Top guest favorite
Cottage in Winthrop
Breakfast included, steps from the beach
4.98 out of 5 average rating, 503 reviews, 4 beds, 1 bath
Aug 16 – 21
Top guest favorite
Condo in Winthrop
Oceanfront with lighthouse-speckled views
4.99 out of 5 average rating, 237 reviews, 3 bedrooms, 4 beds, 2 baths
Sep 5 – 10
Top guest favorite
Condo in Winthrop
Historic penthouse with a private roof deck
4.98 out of 5 average rating, 116 reviews, 3 bedrooms, 4 beds, 1 bath
Aug 31 – Sep 5
Top guest favorite
Condo in Winthrop
Waterfront condo with spectacular ocean views
4.99 out of 5 average rating, 80 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 12 – 17
Superhost
Room in Winthrop
Victorian home near the beach
4.79 out of 5 average rating, 285 reviews, 1 double bed, 1 bath
Nov 1 – 6
Top guest favorite
Apartment in Winthrop
Oceanside community, minutes from Boston
4.96 out of 5 average rating, 112 reviews, 1 bedroom, 1 bed, 1 bath
Aug 16 – 21
Guest favorite
Home in Winthrop
Fireplace and deck, 5 min from beach
4.86 out of 5 average rating, 92 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 15 – 20
Apartment in Winthrop
Top-floor ocean view with private balcony
New place to stay, 2 bedrooms, 2 beds, 1 bath
Aug 22 – 27
Top guest favorite
Home in Winthrop
1880 Victorian manor with ocean views
4.98 out of 5 average rating, 52 reviews, 6 bedrooms, 10 beds, 3.5 baths
Aug 24 – 29
Top guest favorite
Room in Winthrop
Large yard with deck near the beach
4.91 out of 5 average rating, 108 reviews, 1 single bed, 1 bath
Aug 16 – 21
Top guest favorite
Room in Winthrop
Nautical home with harbor views, near Boston
4.97 out of 5 average rating, 433 reviews, 1 queen bed, 1.5 baths
Aug 12 – 17
Top guest favorite
Room in Winthrop
Harbor views near Logan Airport
4.95 out of 5 average rating, 418 reviews, 2 single beds, 1.5 baths
Aug 16 – 21
Guest favorite
Home in Winthrop
Ocean views from a private deck
4.85 out of 5 average rating, 127 reviews, 3 bedrooms, 5 beds, 1 bath
Nov 5 – 10
Top guest favorite
Apartment in Winthrop
Oceanfront with a hot tub and pool
4.96 out of 5 average rating, 280 reviews, 1 bedroom, 1 bed, 1 bath
Aug 15 – 20
Top guest favorite
Apartment in Winthrop
Brick fireplace in a coastal neighborhood
4.95 out of 5 average rating, 19 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 21 – 26
Room in Winthrop
Oceanfront room, 10 minutes from Boston
4.76 out of 5 average rating, 38 reviews, 3 beds, 1 bath
Aug 16 – 21