| Adams House |
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Location: 29 Trident Ave.
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| Aloha Inn - Location: Highlands -
Corner of Cliff and Highland avenues |
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"On June 1 the Aloha at Winthrop Highlands, Mass. will open. It is under the management of Ninette Whitney, formerly of the Argyle. The bracing air and fine views of Winthrop, and its short distance from the city, commend it as a seummer resort."
"Business men especially will find it advisable to choose The Aloha at Winthrop Highlands, Mass., for a summer home. Easily accessible from the city, it yet possesses all the attactiveness of the country and is a spendidly appointed place. Mrs. Charles Wishman will give any details to inquiries."
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| Argyle Hotel |
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Location: Highlands
Corner Grovers and Cliff avenues
Expanded to become Winthrop Arms
"The Argyle Hotel at Winthrop Highlands, Mass., is located in one of the prettiest section of this sea-grit town, and it is an exceedingly desirable place to pass the summer months. It is near the ocean and the bathing beach is the best, and the cuisine is excellent. F. A. Fitz is the proprieter."
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| Boulevard Hotel |
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Location: Beach
400 Mermaid Ave.
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| Cliff House Hotel |
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Location: Highlands
Corner Grovers and Cliff avenues
Demolished: 1963
"Because of its pleasing location directly on the ocean-front at Winthrop Highlands, Mass. The Cliff House is always well patronized. It is reached in twenty minutes by trains from Boston. The service is in keeping with other appointments. Bathing, boating and tennis are a few of the features. For a descriptive booklet and rates, apply to Mrs. Mary J. O'Brien, manager."
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| Colonial Inn / Governor Winthrop Hotel / Inn at Crystal Cove |
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Location: Cottage Hill
600 Shirley St.
"At Winthrop Beach 'The Colonial' has already opened for reception of guests. Under the able management of Mrs. H.H. Cade, who is also proprietress, the coming season there promises to be a success. The location with its variety of views is exceedingly attractive, the cuisine will be excellent."
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| Cottage Park Hotel |
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Location: Cottage Park
"Convenient and Accessible. On the North Shore, commanding a magnficient of Harbor. Fine bathing and boating. New garage. Four miles from Boston by rail, 15 minutes' service, 10 miles by boulevard. Sun parlors, lawns, fine shade trees, outdoor salt-water swimming pool reserved for guests, tennis courts, new Court Golf, grand views of harbor islands and all marine activity. Yachting and boating facilities. Excellent orchestra. Table plentifully supplied with fresh vegetables, fish and fruit. The preparation and serving of sea food a specialty. Write booklet and rates to William W. Gates, Managing Director."
Orlando Belcher (1844-1923) was an entrepreneur in the shoe industry and also a real estate developer in Winthrop. In the early 1870’s he began buying land in the Cottage Park area of Winthrop. In 1887 he purchased the Bartlett Estate and rebuilt the structure doubling its size and converting it to a hotel. The Cottage Park Hotel, and a number of cottages nearby, were a popular summer resort location in the late 1800’s and early 1900’s. After World War I, Belcher retired and sold his property. Business declined and eventually the hotel was raised and the land subdivided. Several of the original cottages still exist.
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| Crest Hall Hotel |
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Location: Winthrop Shore Drive
Corner of Ocean Ave. and Winthrop Shore Drive
""One hundred or more dancing masters from many Eastern cities are in convention at Crest Hall, Winthrop today. It is the twenty-third annual session of the organization know as the American National Association Masters of Dancing, and Oscar Duryea, the president, occupied the chair when the business session was called to order this morning. A number of topics related to grace, deportment and stage and fancy dancing will be taken up during the convention, whihc will last throughout the week."
""One life was lost is the fire which burned two hotels, a hotel annex and six cottages, and caused a lost of about $200,000 at Winthrop Beach last night. Besides the cottages destroyed, several were damaged. Acting Chief Jeremiah C. Blake of the town police said at 3 P.M. that the search had been made all about town and no trace of the missing woman, Mrs. Henry Dumont of Albany N.Y., had been found... The buildings destroyed or damaged... were as follows: Crest Hall Hotel, Ocean View Hotel..."
Built by Fred Hall in 1901 |
| Dearborn Hotel |
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Location: ?
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| The DeOane |
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Location: ?
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| Durbin Hotel |
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Location: Shirley St.
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| Hawthorne Hotel |
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Location: Cottage Hill
Corner of Hillside and Park avenues
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| The Kearsarge |
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Location: Winthrop Highlands
"The most charming summer home, combining seashore and country, on the New England coast, with quick access to Boston. Beautiful ocean view, surf bathing, all outdoor sports, wide veranda, spacious rooms and cusine the best. Terms very reasonable. Send for circular. Thomas J. Ash, Propritor."
"A plesantly situated hotel at Winthrop Highlands, Mass., is The Kearsarge on Highland avenue. It is a first-class place with attractive rooms, good board and reasonable rates."
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| Leighton House |
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Location: Highlands
Corner of Crest and Grovers avenues
"The scene of beauty that attracted the eye at the Leighton house ball Friday evening will long be remembered by the fortunate invitation holders who availed themselves of the opportunity to participate in the opening festivities of the summer season. The popularity of the Leighton was tested to its utmost capacity, and from the commencement to finale enjoyment reigned supreme."
"Winthrop Highlands, Mass. Finest location in Winthrop, at head of Boulevard. House thoroughly renovated and improved. Excellent table. Bowling. Dancing and Card Parties Weekly. Diners arranged for clubs and organizations. Weekend parties accommodated."
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| Hotel Landausea |
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"Since the destruction by fire if Winthrop's two largest hotels, th need of good hotel accommodations has been keenly felt by the town. This demand is about to be fulfilled by the erection of a first-class hotel that will meet all requirements."
Location: Never built
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| Loring Hotel |
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Location: Court Park
""Winthrop Point, Winthrop Centre. Now Open. Reduced rates for June and September. 100 feet from water and in view of all islands and shipping in harbor. 20 nminutes to Boston, with 5-cent fare. 1 minute from Winthrop golf and ball grounds. Stable, telephone, 4000 feet piazza, electric lights, open fireplaces, etc. Special price for long season. For leaflet, with cut of house and all particulars, apply to L. S. Farnsworth, Proprietor, or call and see the coolest, finest spot on North Shore."
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| Nevada House |
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Location: Beach
Corner of Nevada St. and Winthrop Shore Drive
"Winthrop Beach is so near Boston that any worker who desires to spend the summer at the seaside can do so. The Nevada House, under charge of Mrs. A. M. Borsh, will accommodate boarders at reasonable rates."
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| New Winthrop Hotel / Hotel St. Leonards / Great Head Hotel |
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Location: Beach
Sturgis St. between Shirley St. and Winthrop Shore Drive
"This fine hotel has 96 guests' rooms and 12 servants' rooms, bowling alley, billiard hall, large dining-rooms, fine office, etc.: has steam heat, electric lights; is but a minute's walk from the best beach on the Atlantic Ocean; not over 2 minutes from steam station, near steamboat landing; 48,360 ft. land, and extends from Sturgus street to Irwin street; has just been thoroughly overhauled, repainted outside and in, newly papered and put in the best condition; this hotel is within 30 minutes' of Boston and a five-sent fare.; this property can be bought at a bargain. Edward T. Harrington & Co."
"Formerly Hotel St. Leonards, Ocean Spray, Winthrop Mass., 30 minutes' ride from Boston by Revere Beach & Point Shirley Railroad, is now open; it has been renovated and painted inside and out; parlors heated by furnace; fine bathing beach within one minute's walk, a boarding stable in connection, cars stop at the door. Sweetser & Killam. Proprietors."
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| Ocean House |
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Location: Trident Ave.
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| Ocean View Hotel |
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Location: Beach
Corner of Ocean Ave. and Winthrop Shore Drive
Destroyed by fire: October 2, 1908
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| Hotel Puritan |
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Location: Cottage Ave.
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| Sea Breeze Hotel / The Shirley / Hotel Shirley |
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Location: Corner Winthrop Shore Drive and Hawthorn Ave.
"Ocean Spray. Situated directly on the ocean, two minutes walk from the station, twenty fire minutes to Boston. Boating, bathing and fishing. Fine tennis and croquet grounds. For terms and particulars, apply to M. E. Fritz, Proprietor"
Demolished: 1963
219 Winthrop Shore Drive.
Mrs Lena Glasswan |
| Silver Kettle |
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Location: Winthrop Beach
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| Taft's Hotel / Point Shirley |
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Location: Point Shirley
- Taft's Hotel, Point Shirley, Boston Daily Evening Transcript, August 7, 1868
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| Winthrop Arms Hotel |
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Location: Highlands
Corner Grovers and Cliff avenues
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| Winthrop Beach House |
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Location: ? |
| The Woodside |
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Location: ?
E.C. Hall Manager, Boston Evening Transcript - May 24, 1905 |
| The Worcester |
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Location: ? |
| Young's Hotel |
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Location: Beach
Corner of Tewksbury St. and Winthrop Shore Drive
"Young's Hotel at Winthrop Beach, Mass., is pleasantly situated on the State boulevard, fronting the ocean. There is a fine swimming beach and ample opportunities for boating and fishing. The tooms are good and board first-class."
Destroyed by fire: November, 1910
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