Vacation rentals in Winthrop

4.9 out of 5 average rating, 30 reviews

A dining area is presented with multiple wooden chairs surrounding a table set with blue plates and glassware. Large windows open towards the lake, allowing natural light and providing views of the water, while inviting the outdoors in.

Cottage in Manchester

Lakefront cozy cottages w/ dock, canoe & fire-pit!

Situated a few steps from the water of Lake Cobbossee (Cobbosseecontee), with direct views of the sunset. So close to the lake it feels like you are on a boat. The cottage and bunkhouse are welcoming and very cozy. If you prefer a high-end lake house with lots of modern conveniences, this might not be for you, but it may be exactly what you need to relax and forget all your worries for a while. Curl up inside, hang out by the fire pit, swim off the dock or take the canoe out to spot some loons.

The camp is illuminated at night, showcasing its inviting exterior. A large porch wraps around the structure, surrounded by trees, while a fire pit is visible in the foreground, where guests can be seen enjoying the warmth of the fire.

5 out of 5 average rating, 16 reviews

Waterfront | Dock | Fire-pit | Laundry!

Spacious four-season lakefront camp on peaceful Dexter Pond in central ME. Enjoy great fishing, canoeing, stand-up paddle boarding, kayaking, or relax and watch the sunsets and loons from the large porch overlooking the pond. The home is in a great location close to Winthrop Center and Wayne (10 mins to local grocery store/ farmers market) 30 mins to Augusta/airport. Many hiking trails nearby and lots of other areas to explore. It's beautiful in all seasons. Private dock, firepit, and laundry!

4.98 out of 5 average rating, 170 reviews

A spacious private room features a large bed adorned with soft bedding, flanked by modern lamps. Natural light streams in through the door, which opens to a serene outdoor view. A decorative pillow with a sunflower adds a touch of color to the space.

Guest suite in Monmouth

Welcome to The Nest - 1 bed, deck w/bath & parking

Enjoy easy access to entertainment, restaurants & shopping. Historic Cumstom Theater, local Bakery, Bar & pizzeria. Willows Awake and The Vista wedding venues w/tasting rooms. Microbrewery’s Grateful Grains & Van der Brew tap rooms w/food trucks & entertainment. Maine turnpike access for shopping;Freeport LLBean, Portland, Bath, Augusta, Hallowell & Lew/Auburn areas. Tour Bates,Bowdoin, Colby, Thomas & Husson. Golfing, boating, antiques, State Parks, hiking/walking trails,beaches & Festivals.

The exterior of a charming 1900s home is visible, showcasing a light-colored facade with a prominent red door. Sunlight filters through the branches of nearby trees, creating a welcoming ambiance in the front yard.

4.73 out of 5 average rating, 41 reviews

Central downtown & beach area, fish from backyard

Enjoy the beautiful Lakes Region of central Maine! This charming 1900's home is on a quiet street, walking distance to Lake Maranacook town beach, and a minute stroll to Downtown Winthrop. Bring your kayaks and kayak from the backyard to Annabessacook lake! With 4 lakes, hiking trails on Mount Pisgah, boating, winter skiing nearby & ice fishing. Winthrop has all the outdoor fun! 2 bdrms & 1 bath on the 1st level & the entire 2nd level the ideal kids bedroom/hangout. All new furniture & bedding.

4.9 out of 5 average rating, 67 reviews

A large, rugged stone fireplace serves as a focal point in the living area, featuring a sturdy mantel decorated with candles and greenery. A wooden staircase curves next to the fireplace, leading to the upper level. A decorative plant is placed in front of the fireplace.

Home in Monmouth

Spacious Lakeside Comfort - Fall/Winter Wonderland

This spacious home is just steps from the shore of Anabessacook Lake. Here you will enjoy the comfort and luxury of a well-equipped house, surrounded by the best of what Maine has to offer. The Red Top House features an incredible stone fireplace, large screened porch, and stone patio with outdoor fire pit. Bedrooms are comfortable with water views. The kitchen is very well equipped for the whole family. Rental includes use of non-motorized boats and firewood. Ice fishing is steps away!

4.99 out of 5 average rating, 236 reviews

A spacious dome tent is nestled among tall trees, with sunlight filtering through the leaves, creating a warm glow. The forest floor is covered with soft earth and scattered leaves, enhancing the natural surroundings, while the calm ambiance invites visitors to relax and enjoy the scenery.

Island in Monmouth

Hammock Haven Island Dome

The Hammock Haven Island Dome looks at sunsets on Annabessacook Lake. Sleep comfortably, cook your favorite meals, hammock nap on a dock in the water, bask in the glow of the fire or wood stove, hear the calls of the loons, play on the rope swing, canoe, kayak, or paddle board the lake, explore the trails of this 14 acre wooded island, and then repeat as needed. We greet you at our shoreside dock and help you settle into island-life. Enjoy super clean, Superhost, Maine Guide hospitality.

4.98 out of 5 average rating, 141 reviews

A spacious bedroom features a large bed with blue bedding against a dark blue accent wall. Two bedside lamps provide soft lighting. A comfortable leather armchair is positioned next to a small nightstand, which holds a tissue box and a framed print.

Home in Hallowell

Hilltop Retreat with A/C, Hot Tub & Sauna

Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub or infrared sauna, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

4.81 out of 5 average rating, 120 reviews

The kitchen features wooden cabinets and a granite countertop. A round dining table with four chairs is situated centrally. Stainless steel appliances, including a refrigerator and a stove, are visible, along with various kitchen utensils and supplies arranged on the countertop.

Apartment in Augusta

Downtown Augusta - 2 Bedroom - Newly renovated!

Located at the heart of downtown Augusta, this 2 bedroom apartment is a wonderful choice when visiting Augusta Maine with another couple or if you just want more room then your average hotel! This 2nd floor apartment comes fully furnished with brand new furniture, supplies and bedding! The apartment has keyless entry via a keypad with each guests receiving a unique pin. There is free parking and laundry available on site. Enjoy a stylish experience at this centrally-located place.

4.97 out of 5 average rating, 191 reviews

A serene landscape captures a vibrant sunset reflected on calm water. The sky displays shades of orange and pink, blending into deep purple hues, while the silhouette of trees lines the horizon. The tranquil scene conveys a peaceful natural setting.

Loft in West Gardiner

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment above our garage. 15 minutes to Gardiner/Augusta, 15 minutes to I95/295. Less than one hour from Portland. Sit by the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and play. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Superhost

A warm cabin interior features wooden walls and a high ceiling. A comfortable sofa is complemented by decorative pillows. A wooden ladder leads to a loft area. A TV is positioned on a rustic console, and a dining table sits near a window, providing natural light.

Cabin in Monmouth

4.86 out of 5 average rating, 37 reviews

The Woodland Lodge

Looking for a cozy family-friendly get away in the beautiful woods with access to a shared beach on Annabessacook Lake, look no further than The Woodland Lodge. Located in Monmouth ME, the cabin is close to the public boat launch for Cobbosseecontee Lake and Whittier Woods trails. It is 30 minutes to Augusta Regional airport, 1 hour to Portland Jetport, and 90 minutes to Sugarloaf. Enjoy the peaceful woods, shared beach access, and beautiful hiking trails nearby!

4.97 out of 5 average rating, 77 reviews

A charming blue cabin stands amidst greenery, featuring a white porch with steps leading up to the entrance. Adirondack chairs are arranged around a fire pit in the grassy yard, providing a welcoming outdoor space for relaxation.

Cabin in Winthrop

Quaint & cozy cabin in beautiful wooded setting

Kick back and relax in this calm, stylish space. Less than 15 minutes to Augusta, and an hour from Portland! Close to many amenities, but far enough out to enjoy nature. The cabin sits on 33 acres, with fields and trails. The cabin itself has Wi-Fi, cable tv, a lofted queen bedroom, all of which have been recently updated. Outdoor amenities include BBQ grill, and lakes and ponds in close proximity.

Superhost

A charming cottage is nestled among trees along the lakefront, featuring a sloped roof and large windows. A wooden dock extends into the water, with steps leading up to the home, providing easy access to the serene surroundings.

5 out of 5 average rating, 4 reviews

Serene Lakeside Retreat

Relax with the family at this peaceful lakefront retreat on Cobbosseecontee Lake. Lovingly remodeled with care, this cozy 2-bedroom cottage blends Maine cabin charm with modern updates. Enjoy a full kitchen, spacious living area, two baths, a screened porch, and a deck with stunning lake views. Kayaks included! Unwind, explore, and make lifelong memories at this beautiful waterfront escape.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Winthrop vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Winthrop

4.81 out of 5 average rating, 53 reviews

Private room in Monmouth

Peaceful Room in Historic House on Mill Pond

Superhost

Private room in Hallowell

4.85 out of 5 average rating, 251 reviews

Room A - 1st floor, hot tub, gym & sauna

A quaint cottage is surrounded by lush greenery and well-maintained landscaping. A gravel path leads to the cottage, which features a welcoming porch and a charming wheel decoration. Trees provide a natural backdrop, enhancing the serene atmosphere of the setting.

Cabin in Readfield

5 out of 5 average rating, 4 reviews

Camp Hope

A spacious deck offers lounge chairs for relaxation, overlooking the serene Annabessacook Lake framed by lush greenery. A dining set is also visible, inviting outdoor meals, while additional chairs provide comfortable seating for enjoying the water views.

4.57 out of 5 average rating, 14 reviews

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!

A compact camper adorned with a distinctive black and silver exterior is positioned on a paved area surrounded by trees. Two folding chairs are arranged outside, inviting relaxation. An awning extends from the side, providing shade for outdoor enjoyment.

Camper/RV in Livermore Falls

5 out of 5 average rating, 5 reviews

The Moon Root - Kut Away

4.98 out of 5 average rating, 56 reviews

The exterior of a two-story house is shown, featuring a welcoming porch adorned with planters and flowers. A paved driveway leads to a two-car garage mounted with wooden doors. Surrounding greenery and a clear blue sky enhance the inviting atmosphere of the residence.

Guest suite in Hallowell

Private, Hallowell In-Law Apartment