Travels » Vacation Rentals » United States » Massachusetts » Winthrop

Vacation Home Rentals in Winthrop, Massachusetts

Vacation Home Rentals in Winthrop, Massachusetts

Beautiful Waterfront On Tree-Lined Street, Sunset Views Abound!
Beautiful Waterfront on Tree-lined Street, Sunset Views Abound!
Apartment with 2 bedroom(s), 1 bathrooms(s), sleeps 6
0.7 miles to Winthrop
Winthrop, 2152
Newly renovated, this charming home was built in 1920 and we are the third owners to live here. Hardwood floors throughout, waterfront and...

from 1,095 USD

Weekly


View Details
Stay By The Big City In Small Town Comfort
Stay by the Big City in Small Town Comfort
Condo with 4 bedroom(s), 1 bathrooms(s), sleeps 8
0.4 miles to Winthrop
Winthrop, 2152
You'll feel right at home in this 1,350 s.f. plus flexible rental in Winthrop by the Sea! Don't squeeze yourselves into small quarters and dine...

from 2,800 USD

Weekly


View Details

Vacation Home Rentals in the Winthrop, Massachusetts Area

Boston Vacation Rentals - La Cappella Suites
Boston Vacation Rentals - La Cappella Suites
Bed and breakfast
3.8 miles to Winthrop
Boston, Massachusetts, 02113
La Cappella Suites, a North End bed and breakfast inn, is your home away from home in Boston. Located in the heart of 'Little Italy', the city's...
View Details
Boston Vacation Rentals - The Golden Slipper - Boston's B&B 'Afloat'
Bed and breakfast
3.8 miles to Winthrop
Boston, Massachusetts, 02110
The Golden Slipper, Boston’s b&b “Afloat” is a 1984 Catalina Chris Craft. The 40’ Yacht is located at Lewis Wharf, in the heart of historic...
View Details
Boston Vacation Rentals - The Charles Street Inn
Bed and breakfast
4.5 miles to Winthrop
Boston, Massachusetts, 02114
Gas street lamps light your way past unique boutiques and antique stores as you stroll down historic Charles Street, where our Boston luxury bed &...
View Details
Boston Vacation Rentals - Clarendon Square Bed And Breakfast - A Boston Inn
Bed and breakfast
5.4 miles to Winthrop
Boston, Massachusetts, 02118
If you are looking for a unique and historic experience in Boston's center, you will enjoy Clarendon Square’s style, history, and amenities. Our...
View Details
Cambridge Vacation Rentals - Antrim House Bed & Breakfast
Bed and breakfast
6.4 miles to Winthrop
Cambridge, Massachusetts, 02139
Whether you're visiting Cambridge for pleasure, business, or academia, Antrim House is the perfect location. Subways and buses are easily...
View Details
Cambridge Vacation Rentals - Harding House
Bed and breakfast
6.4 miles to Winthrop
Cambridge, Massachusetts, 02139
Come and experience a refreshing alternative to major hotels at the Isaac Harding House in Cambridge. Let our unique recently remodeled 1860's...
View Details
Boston Vacation Rentals - Abigayle's Bed And Breakfast
Bed and breakfast
6.6 miles to Winthrop
Boston, Massachusetts, 02215
Set on a quiet, tree lined street adjacent to Kenmore Square and near Boston University, this elegant 4 story brownstone was built in 1896. The...
View Details
Boston Vacation Rentals - The Gryphon House
Bed and breakfast
6.6 miles to Winthrop
Boston, Massachusetts, 02215
The Gryphon House is a luxurious bed and breakfast housed in a turn-of-the-century brownstone within easy walking distance to most of the...
View Details
Brookline Vacation Rentals - The Samuel Sewall Inn
Bed and breakfast
7.6 miles to Winthrop
Brookline, Massachusetts, 02446
Built in 1886, as a private residence, The Samuel Sewall Inn boasts beautiful Victorian accommodations, in a restored Queen-Anne home, with...
View Details
Somerville Vacation Rentals - Meacham Manor
Bed and breakfast
7.6 miles to Winthrop
Somerville, Massachusetts, 02144
Centrally located in the heart of Somerville's most celebrated hotspot, Davis Square, Meacham Manor Bed and Breakfast is a wonderful inn known for...
View Details
Somerville Vacation Rentals - Morrison House Bed & Breakfast
Bed and breakfast
7.6 miles to Winthrop
Somerville, Massachusetts, 02144
Whether you're in the Boston area for business, sightseeing, or visiting your college-student son or daughter, this charming, 12-room, Italianate,...
View Details
Lynn Vacation Rentals - Diamond District Breakfast Inn
Bed and breakfast
7.7 miles to Winthrop
Lynn, Massachusetts, 01907
This 1911 Georgian style mansion sits on ½ acre in Boston's North Shore, which is known as 'Lynn's Diamond Historical District.' Designed by...
View Details
Cambridge Vacation Rentals - A Friendly Inn At Harvard
Bed and breakfast
7.8 miles to Winthrop
Cambridge, Massachusetts, 02138
Minutes from Harvard University. Library and Pool Across the Street. Minutes from Harvard Square in Cambridge. Convenient Cambridge location to...
View Details
Boston Vacation Rentals - Taylor House Bed & Breakfast
Bed and breakfast
7.9 miles to Winthrop
Boston, Massachusetts, 02130
Taylor House, a gracious sixteen room Victorian home in Boston’s Jamaica Plain section, was built around 1853 for George W. Taylor, an...
View Details
Boston Vacation Rentals - Casa Do Zequita Bed & Breakfast
Bed and breakfast
9.3 miles to Winthrop
Boston, Massachusetts, 02135
Casa do Zequita, has three comfortable guest rooms, a beautiful living room for your enjoyment. Our breakfasts are served in the kitchen & are...
View Details
Marblehead Vacation Rentals - Fox Pond Bed & Breakfast
Bed and breakfast
10.3 miles to Winthrop
Marblehead, Massachusetts, 01945
Rated #1 in Marblehead by TripAdvior Nestled amongst tall oaks and ensconced in beautiful English gardens, Fox Pond b&b provides a welcome...
View Details
Marblehead Vacation Rentals - Harbor Light Bed And Breakfast Inn
Bed and breakfast with 21 bedroom(s)
10.3 miles to Winthrop
Marblehead, Massachusetts, 01945
Federalist mansions in heart of historic harbor district of fine shops, galleries, restaurants and waterfront. Fireplace rooms, canopy beds,...
View Details
Marblehead Vacation Rentals - Harborside House
Bed and breakfast with 2 bedroom(s)
10.3 miles to Winthrop
Marblehead, Massachusetts, 01945
Harborside House offers gracious accommodations and warm hospitality in a great location. This handsome 1850 home in the historic district...
View Details
Marblehead Vacation Rentals - Jersey Hill Bed And Breakfast
Bed and breakfast with 3 bedroom(s)
10.3 miles to Winthrop
Marblehead, Massachusetts, 01945
Located just a short walk from Marblehead's historic 'Old Town', harbor and beaches, the Jersey Hill Bed & Breakfast is an elegantly decorated...
View Details
Marblehead Vacation Rentals - One Kimball At Marblehead Light
Bed and breakfast
10.3 miles to Winthrop
Marblehead, Massachusetts, 01945
One Kimball is a bed and breakfast situated at the base of the Lighthouse on Marblehead Neck. Enjoy panoramic views of the harbor, Abbot Hall,...
View Details
Marblehead Vacation Rentals - Pheasant Hill Inn Bed And Breakfast
Bed and breakfast
10.3 miles to Winthrop
Marblehead, Massachusetts, 01945
Welcome to Marblehead Marblehead is a truly historic and attractive New England town. Incorporated in 1649, its landscape today features more...
View Details
Marblehead Vacation Rentals - The Seagull Inn Bed And Breakfast
Bed and breakfast
10.3 miles to Winthrop
Marblehead, Massachusetts, 01945
On beautiful Marblehead Neck, sun-drenched and comfort-filled suites greet you in this old New England inn which has been totally restored with...
View Details
Arlington Vacation Rentals - An American Bed & Breakfast
Bed and breakfast
10.4 miles to Winthrop
Arlington, Massachusetts, 02476
An American Bed & Breakfast in historic Arlington, Massachusetts, a town nestled between Cambridge and Lexington, is a home of architectural and...
View Details
Salem Vacation Rentals - The Salem Inn
Bed and breakfast
10.7 miles to Winthrop
Salem, Massachusetts, 01970
Located in the heart of one of America's oldest seaports, the Salem Inn comprises three historic homes offering accommodations rich in history...
View Details
Newton Vacation Rentals - Park Lane Bed And Breakfast
Bed and breakfast
11.8 miles to Winthrop
Newton, Massachusetts, 02459
Only 20-25 minutes from Downtown Boston by T light rail, the Park Lane is just west of the city in tree-lined Newton. Built in 1910, the Baronial...
View Details
Beverly Vacation Rentals - Gordon's 1841 House Bed & Breakfast
Bed and breakfast
13.9 miles to Winthrop
Beverly, Massachusetts, 01915
Historical home conveniently located in downtown Beverly, 17 miles north of Boston in the Cape Ann Area. Just over the bridge from Salem. One mile...
View Details
Lexington Vacation Rentals - Mary Van's 'My Old House' Bed And Breakfast
Bed and breakfast
14 miles to Winthrop
Lexington, Massachusetts, 02421
Lexington, Massachusetts, a town familiar to Americans across the nation, its name passed from generation to generation through stories depicting...
View Details
Lexington Vacation Rentals - Morgan's Rest Bed & Breakfast
Bed and breakfast
14 miles to Winthrop
Lexington, Massachusetts, 02421
Morgan's Rest Bed and Breakfast is located in Lexington, Massachusetts. We are west of Boston, but very convenient for visitors traveling into the...
View Details
Gloucester Vacation Rentals - 6 Bedroom, Waterfront Cottage With Boat Access
Cabin with 6 bedroom(s), 2 bathrooms(s), sleeps 12
23.2 miles to Winthrop
Gloucester, Massachusetts, 01930
Discover life's simple pleasures above the waters edge overlooking rustic Pierce Island and Wingaersheek Beach. Take in the sweeping shoreline...

from 257 USD

daily


View Details
Gloucester Vacation Rentals - Bed & Breakfast Reservations
Bed and breakfast
23.2 miles to Winthrop
Gloucester, Massachusetts, 01930
Bed & Breakfast Reservations is a Massachusetts-based Reservation Service, providing reservations in carefully selected B&B's, small Inns and...
View Details
Gloucester Vacation Rentals - Julietta House Bed & Breakfast
Bed and breakfast
23.2 miles to Winthrop
Gloucester, Massachusetts, 01930
Whether visiting Cape Ann for a Weekend Getaway, Business Retreat, Family Reunion or to visit friends or attend a Wedding; all will enjoy the...
View Details
Gloucester Vacation Rentals - Lanes Cove House
Bed and breakfast
23.2 miles to Winthrop
Gloucester, Massachusetts, 01930
Lanes Cove House is an 1800s Victorian, quaint, cozy and comfortable. Enjoy pre-breakfast coffee in your room if you like, followed by a...
View Details
Gloucester Vacation Rentals - Waterfront With Pool .. Comf Home & Studio Apt
House with 3 bedroom(s), 2 bathrooms(s), sleeps 6
23.2 miles to Winthrop
Gloucester, Massachusetts, 01930
Located on Cape Ann, this comfortable 3 bedrm home , is a great space to share with your family and/or friends. Shared by both the house and apt....

from 100 USD

daily


View Details
Scituate Vacation Rentals - Scituate Beach Home
Vacation rental with 3 bedroom(s), 1 bathrooms(s)
16.9 miles to Winthrop
Scituate, Massachusetts, 02066
We have a furnished three bedroom colonial just down the street from Sand Hills Beach. The house a three season front porch with a nice sitting...
View Details
Gloucester Vacation Rentals - Beachfront Apartment On Historic Rocky Neck
Vacation rental with 1 bedroom(s), 1 bathrooms(s)
23.2 miles to Winthrop
Gloucester, Massachusetts, 01930
Second floor apartment; direct waterfront. Beautiful, unobstructed ocean views; on a clear day you can see to Boston. Watch ships appear on the...

from 86 USD


View Details
Gloucester Vacation Rentals - Private Wingaersheek Beach Vacation Home
Vacation rental with 4 bedroom(s), 2 bathrooms(s)
23.2 miles to Winthrop
Gloucester, Massachusetts, 01930
Located in the Private Section of Wingaersheek Beach (Coffin's Beach)and just a 3 minute walk to to the beach. Enjoy this totally renovated 4...

from 381 USD


View Details
Scituate Vacation Rentals - Oceanside Inn Of Scituate
Bed and breakfast
16.9 miles to Winthrop
Scituate, Massachusetts, 02066
The Oceanside Inn of Scituate is the only Bed and Breakfast located right on the ocean in the charming seaside town of Scituate, Massachusetts....
View Details
Gloucester Vacation Rentals - Wingaersheek's Cool Cove: Beachfront And Views!
Vacation rental with 4 bedroom(s), 3 bathrooms(s)
23.2 miles to Winthrop
Gloucester, Massachusetts, 01930
Sun when you want it. Shade when you need it. Cool Cove has it all. Jutting high above Wingaersheek Beach on a promontory from which it seems that...

from 737 USD


View Details
Gloucester Vacation Rentals - Ocean Front Home At Private Wingaersheek Beach
Vacation rental with 4 bedroom(s), 3 bathrooms(s)
23.2 miles to Winthrop
Gloucester, Massachusetts, 01930
OCEANFRONT /Steps to the beach. Nantucket style contemporary with panoramic views of ipswich bay, crane beach,annisquam light house, and nh/maine....

from 929 USD


View Details
Harborfront Villa, Charming Mix Of Contemporary And Turn Of The Century Elegance
Villa with 4 bedroom(s), 1.5 bathrooms(s), sleeps 8
1.1 miles to Winthrop
East Boston
The Villa at Eastie overlooks the harbor and shipping channels, early morning lobstermen can be seen from the sunroom hauling their traps, as well...

from 2,500 USD

Weekly


View Details
Best Harbor/Water Views 3Br Charming 1847 Brick W/Giant Deck, Great Location
Apartment with 3 bedroom(s), 1.5 bathrooms(s), sleeps 6
2.6 miles to Winthrop
Boston, 2128
Located in historic 1847 brick bowfront brownstone, this unique artist-owned property features original details like exposed brick, hardwood...

from 1,350 USD

Weekly


View Details
Beautiful Houseboat In Downtown Boston!!
House_boat with 3 bedroom(s), 1 bathrooms(s), sleeps 8
2.8 miles to Winthrop
Boston, 2128
If you are planning a visit to Boston consider staying on our lovely houseboat 'Motif No. 2'! Located in the Boston Harbor Shipyard in Boston...

from 1,000 USD

Weekly


View Details
Views Of Boston Harbor
Apartment with 2 bedroom(s), 2 bathrooms(s), sleeps 4
2.8 miles to Winthrop
Boston (East), 2128
Located in Jeffries Point, East Boston. East Boston is one of Boston's mostly residential areas that maintains a genuine neighborhood atmosphere....

from 1,200 USD

Weekly


View Details
Downtown Views & Parking Laundry In Unit Quite & Enjoyable Close To The Subway
Apartment with 2 bedroom(s), 1 bathrooms(s), sleeps 3
3.1 miles to Winthrop
East Boston, 2128
Wonderful Boston location right on the harbor you can easily walk to everything including public transportation, water taxi's beautiful Piers Park...

from 750 USD

Weekly


View Details
Harbor View 2Nd Floor Apartment With Parking In Quite Neighborhood
Apartment with 1 bedroom(s), 1 bathrooms(s), sleeps 4
3.1 miles to Winthrop
Boston, 2128
Jeffries Point East Boston is a lovely residential neighborhood in Boston. The airport is less than a mile away but you would never know it since...

from 1,200 USD

Weekly


View Details
2 Bedroom Condo In The Historical North End Of Boston Ma! Near Freedom Trail!
Condo with 2 bedroom(s), 1 bathrooms(s), sleeps 4
3.6 miles to Winthrop
Boston, 2113
Located in a quiet courtyard with the charm of Old Italy,our two-bedroom condo is the perfect place for a fun-filled vacation or a business trip.A...

from 995 USD

Weekly


View Details
Back Bay Taditional Brownstone, Downtown Boston
Apartment with 1 bedroom(s), 1 bathrooms(s), sleeps 6
3.6 miles to Winthrop
Boston, 2116
Modern renovations enhance the charm of this original Boston brownstone, located between Exeter and Fairfield Streets in the Back Bay. Close to...

from 1,265 USD

Weekly


View Details
Beautiful One Bedroom Condo In Full Service Building
Condo with 1 bedroom(s), 1 bathrooms(s), sleeps 2
3.6 miles to Winthrop
Cambridge, 2142
We meet the highest quality standards for luxury living. Located in Boston, everything you would ever need at your fingertips. We provide you with...

from 1,500 USD

Weekly


View Details