We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes and Apartments Windsor, ME and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 16 Rentals in the Windsor Area
    loading...
    Don't let other travellers get your favourite Windsor area holiday rental. You're so close to securing your perfect getaway. Book today.
    Sort by

    The following rentals are within 25 kilometres of Windsor, Maine.

    From
    $2,048
    / Week
    View Details
    1 / 14
    5 of 5 stars (2) Excellent
    Belgrade
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (2) Make Enquiry
    From
    $195
    / Night
    Payment Protection
    View Details
    1 / 46
    5 of 5 stars (1) Excellent
    Hallowell
    8 Bedrooms / 8 Bathrooms / Sleeps 19
    Overview Reviews (1) Make Enquiry
    From
    $659
    / Night
    Payment Protection
    View Details
    1 / 20
    5 of 5 stars (1) Excellent
    Manchester
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    From
    $186
    / Night
    Payment Protection
    View Details
    1 / 18
    Vassalboro
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Washer
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Gorgeous year round lake front home on Webber Pond. Floor plan with a commanding view of the lake. Fully equipped kitchen. Water from well - no need to bring drinking water. This Rental has the amenities including furnishings, bedding, and TV's. Rinnai heating system, gas grill, table and chairs.... View all property information
    Make Enquiry
    Location Information
    Vassalboro, Maine 04989
    From
    $260
    / Night
    Payment Protection
    View Details
    1 / 21
    Jefferson
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Lakeside Cottage on Damariscotta Lake in Jefferson Maine. 2 bedroom 1 1/2 baths, separate deck right on the edge of the lake. Enjoy fishing, boating, swimming, or any of the other lakeside activities that you can imagine. Damariscotta Lake is a large pristine lake in the mid-coast Maine area.... View all property information
    Make Enquiry
    Location Information
    Jefferson, Mid Coast Maine 04348
    From
    $298
    / Night
    Payment Protection
    View Details
    1 / 29
    Jefferson
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy this quaint, lovely pine post and beam year-round lake house. It is located near the end of a private, secluded country gravel road about a quarter mile and far from mundane tourist traps. It is nestled amongst old growth pine trees right on the water's edge of Damariscotta Lake in... View all property information
    Make Enquiry
    Location Information
    Jefferson, Mid Coast Maine 04348
    From
    $208
    / Night
    View Details
    1 / 3
    Liberty
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Fully equipped year-round waterfront home on Cargill Pond, in Liberty, Maine. Located near Belfast and midcoast locations. Cool woods and sunny swimming area. 5 kayaks and 1 canoe. Great fishing. Fully equipped kitchen, 1.5 bathrooms, washer and dryer, satellite television upstairs and... View all property information
    Make Enquiry
    Location Information
    Liberty, Mid Coast Maine 04949
    From
    $104
    / Night
    View Details
    1 / 12
    Gardiner
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Your own beautiful Island !!! We believe everyone has dreamed for having one. Thi little gem can be completely yours during your stay here . Little Diamond Island is 1/4 acre which is located in Lake Cobbossee in West Gardiner. About 20 minutes to capital City Augusta & also very close to the... View all property information
    Make Enquiry
    Location Information
    Gardiner, Maine 04345
    From
    $260
    / Night
    View Details
    1 / 10
    Belgrade
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    A unique 2 level, year round home on Great Pond. Situated on the eastern shore in Hatch Cove, the sunsets are incredible. The home is 40 feet from the waters edge with 110 ft of frontage. Children can enjoy the 14 ft wide sandy beach area for safe play. The open concept first level has... View all property information
    Make Enquiry
    Location Information
    Belgrade, Maine 04917
    From
    $349
    / Night
    View Details
    1 / 15
    Belgrade
    3 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This will soon become a family tradition – Visit during summers – enjoy at Pinkham’s Cove at Great Pond in the Belgrade (Lakes), in Maine!! Area is highly known as inspiration for story & film at Golden Pond. Seven beautiful Inter-connected lakes features boating, water ski, fishing, swimming and... View all property information
    Make Enquiry
    Location Information
    Belgrade, Maine 04917
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    $195
    / Night
    View Details
    1 / 13
    Liberty
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Grill
    • Internet Access
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Nature View Cabin is located on pristine, private and lush Lake St George in Liberty, Maine. The location is perfect -- quiet but still close to stores, ice cream and state park/boat launch. Enjoy swimming, kayaking, fishing, island hopping and more in the clean and clear lake. The property... View all property information
    Make Enquiry
    Location Information
    Liberty, Mid Coast Maine 04949
    From
    $150
    / Night
    View Details
    1 / 11
    Augusta
    2 Bedrooms / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Fireplace
    • Grill
    • Satellite TV
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Dramatically set on the side of a mountain, overlooking a sparkling clean, spring-fed 12-acre lake, our cottage is perfect for honeymooners or nature lovers-- or anyone who appreciates peace and quiet. It features a high deck facing our 200 feet of natural lake frontage with dock and canoe. In... View all property information
    Make Enquiry
    Location Information
    Augusta, Maine 04330
    From
    $130
    / Night
    View Details
    1 / 8
    Liberty
    4 Bedrooms / 2 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Grill
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Immaculate, peaceful, picturesque 4 bedroom + loft cottage nestled on beautiful Lake St. George with a nearby boat launch. Just 110 feet from the Lake with 400 foot frontage. Enjoy swimming, boating, sailing Kayaking and canoeing. There is a dock and float. Enjoy the Loons as they swim by and... View all property information
    Make Enquiry
    Location Information
    Liberty, Mid Coast Maine 04949
    From
    $163
    / Night
    View Details
    1 / 7
    Washington
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This lovely 2 bedroom (master bedroom downstairs; loft) cottage is the perfect place for the perfect vacation. Situated on the edge of our 8 acre bluebery field and surrounded by over 100 acres of woodland, it is your place for peace and solitude after a busy day in Camden (or Rockland), just 25... View all property information
    Make Enquiry
    Location Information
    Washington, Mid Coast Maine 04574
    From
    $254
    / Night
    View Details
    1 / 32
    Liberty
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    If you're looking for the perfect, peaceful vacation cottage on a pristine Maine lake, Moon Loon on Lake St. George, Liberty, is right for you. The owner is Colorado children's book author, illustrator, and literary agent, Sandy Ferguson Fuller, and her original picture book, MOON LOON, was... View all property information
    Make Enquiry
    Location Information
    Liberty, Mid Coast Maine 04949
    From
    $260
    / Night
    Payment Protection
    View Details
    1 / 20
    China
    3 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Private Fishing...
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Situated right on Threemile Pond this cozy setup immediately invites a peaceful and private lakeside vacation. The main cottage has a master bedroom with a queen bed, second bedroom with a twin bed and a full size futon, a full kitchen, a ¾ bath and sleeps up to 5. The bunk house has a kitchen, a ¾... View all property information
    Make Enquiry
    Location Information
    China, Maine 04358