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Winthrop Vacation Rentals

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    $231 Average
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    Don't let other travelers get your favorite Winthrop area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 19 Rentals in Winthrop
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    Winthrop
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Winthrop
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Cobbossee Lake House Rental, Winthrop, Maine1 / 16
    (10)Excellent
    Winthrop
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winthrop
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Central Heating
    • Grill
    • Waterfront
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to a quiet, lakefront getaway and explore the beautiful Maine outdoors from this 2-bedroom, 1-bathroom Winthrop vacation rental house that sleeps 4. Nestled against a sandy 170-foot beachfront, this south-facing home offers panoramic views overlooking Annabessacook Lake, a well-appointed...
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    Winthrop, Maine 04364
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Charming Lakefront Cabin, Great View, Private Dock1 / 22
    (3)Very good
    Winthrop
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Porch
    • Grill
    • Washer
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming log cabin on a beautiful 12-mile long lake in Central Maine with great room and front porch. This cabin was built in 1930 (by my grandfather) and recently updated. It is full of character and will give you a fantastic "Maine" experience. One bedroom with a double bed and one with 2 twin...
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    Winthrop, Maine 04364
    Cabin - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lakefront Retreat with Two Cottages and Dog Friendly1 / 24
    (6)Very good
    Winthrop
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • DVD Player
    • Grill
    • Satellite TV
    • Patio
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Winthrop, Maine 04364
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Winthrop
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
    • Parking
    • Satellite TV
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Winthrop, Maine 04364
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Winthrop
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Satellite TV
    • Patio
    • DVD Player
    • Internet Access
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Winthrop, Maine 04364
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The following rentals are within 10 miles of Winthrop.
    East Winthrop
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Grill
    • Washer
    • Patio
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful year around comfortable 2700 square foot lakefront home on Cobbossee Lake. Your family and friends will love this retreat on the shores of Cobbossee Lake! After watching a magnificent sunrise, enjoy lazy afternoons on the water with the help of a private dock, kayaks, a canoe, lakefront...
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    East Winthrop, Maine 04364
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Maple Hill Farm Inn1 / 46
    (1)Excellent
    Hallowell
    8 Bedrooms, 8 Bathrooms, Sleeps 19 Quick View
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    • Hot Tub
    • Air Conditioning
    • Sauna
    • Internet Access
    • DVD Player
    • Patio
    • Mountain Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 16, 2013
    My husband and I spend 4 nights at this beautifully located, tranquil and inviting Bed and Breakfast. We very much enjoyed the very sincere hospitality and personal attitude of...
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    About this property
    In the Augusta area, Maple Hill Farm is in nearby Hallowell just 4 miles from I-95 Augusta Exit 109 on acres of country serenity. Maine's 1st certified “Environmental Leader” green lodging boasts the unique combination of many of the amenities of a quality hotel with the comfort of a quiet country...
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    Location Information
    Hallowell, Maine 04347
    Private Room - 8 Bedrooms, 8 Bathrooms, Sleeps 19
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    Litchfield
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Washer
    • Sauna
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine a place that inspires freedom and joy, relaxes you and energizes your spirit. Sounds good? Isn't it?. Well, it's right here, and it is waiting for you to Escape, to Relax and to Dream. At the Tacoma Lakes Villa in Maine, time stops. It has another meaning. You have for closest neighbors a...
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    Location Information
    Litchfield, Maine 04350
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Villa on Cobbossee Lake, private beach, lake view,1 / 20
    (1)Excellent
    Manchester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Waterfront
    • Washer
    • Satellite TV
    • Grill
    • DVD Player
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxurious villa, sleeps 6 - 8, private beach, canoe, pool table, WiFi. If you are looking for an absolute quiet surrounding and beauty with unlimited privacy, this is the place. It is located on a point at the lake. The sandy beach is 100 feet from the house Private beach with 1500 feet of...
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    Location Information
    Manchester, Maine 04345
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Litchfield
    4 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Washer
    • Waterfront
    • Grill
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 4BR house on Tacoma Lakes House 50' from water, breathtaking views Not a busy lake, 3 spring fed lakes joined by two bridges Brand new private dock , bring your boat Wifi / New 4K Smart TV / Alarm System Screened in Porch with peaceful views Lake watersports: Skiing, tubing, kayak,...
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    Litchfield, Maine 04350
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 10
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    Leeds
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Waterfront
    • Porch
    • Washer
    • Parking
    • Grill
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy the beautiful Androscoggin Lake area in our classic 900 sq. ft. Maine cottage. The cottage has a working kitchen, bath with flush and shower, living room with a queen size sleeper sofa, downstairs bedroom with a queen bed, loft with three twin beds and play area that includes a TV and...
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    Leeds, Maine 04263
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Leeds
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy the beautiful Androscoggin Lake area in our classic 900 sq. ft. Maine cottage that comfortably sleeps 6. The cottage is located on 25 private acres with a large beach and boat facilities. Cottage contains a fully equipped kitchen kitchen,bath with flush and shower, living room with a...
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    Location Information
    Leeds, Maine O4263
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    DUCK INN - WAYNE, MAINE | ON DEXTER POND | KAYAKING, FISHING, SWIMMING, BIRDING1 / 29
    (2)Excellent
    Wayne
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Terrace
    • Balcony
    • Wi-Fi
    • DVD Player
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 26, 2015
    My family and I had such a wonderful time at the Duck Inn. Words cannot adequately capture the tranquility of this beautiful house on a picturesque pond . The house itself was...
    Reviewed September 2, 2013
    This place was everything I wanted. My husband wanted to rent a "cabin" or "cottage" on a lake. He also likes to camp - I do not! This house was well...
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    About this property
    DUCK INN - Wayne Maine Saturday to Saturday full weeks in July and August. You can see more pictures on our Facebook page: https://www.************/DuckInnVacationRentalWayneMaine/ Listen to the Loons. Watch the lake smoke drift. Take in the colors of the sunrise. Breathe. Relax. Renew. De-stress....
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    Location Information
    Wayne, Maine 04284
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Monmouth
    5 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Waterfront
    • Patio
    • Balcony
    • Wi-Fi
    • Washer
    • Grill
    • Secure Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lake Front property including two sets of docks that enable access to beautiful Lake Cobbossee, a nine mile beauty. Currently only two weeks still available, Mid July and Mid August. Two floors with 5 bedrooms. 1 Single bed, 2 queens, 2 sets of bunk beds. A great spot to bring the entire family....
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    Location Information
    Monmouth, Maine 04259
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 11
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    Wayne
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The 3000 sq foot home is a delightful base for activities during all four seasons. Or stay at Paradise on a Lake while you visit the local colleges and universities, all within an hour of the property. Much more comfortable than a hotel for a family, an extended family, or a couple looking to get...
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    Location Information
    Wayne, Maine 04284
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Leeds
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Outdoor Dining Area
    • Porch
    • DVD Player
    • Parking
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax after a day of adventure in our newly updated 900 sq.ft. lakefront family friendly cottage. Conveniently located just steps from a beach, 50 minutes to the ocean and outlet shopping, and 20 minutes to Augusta, Maine's state capital. Designed to keep the classic 'Maine cottage' feel but with...
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    Location Information
    Leeds, Maine 04263
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Winthrop Flight and Weather Info
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    73° 54°
    August
    65° 46°
    September
    51° 35°
    October
    39° 26°
    November

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