Vacation rentals in Winthrop

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Top-rated vacation rentals in Winthrop

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite
The exterior of the cottage is shown, featuring a modern design with gray siding and large windows that provide views of the surrounding landscape. Sturdy steps lead up to the entrance, and the lush green space is dotted with stones and trees.
Cabin in Jefferson
4.88 out of 5 average rating, 129 reviews

Loon Lodge

Located on beautiful Damariscotta Lake, "Loon Lodge" is a rustic cabin from another era. Fall asleep to the sound of crickets and frogs and wake every morning to the call of the lake's many loons. The cabin is 30 minutes from Augusta and 15 minutes from Damariscotta. Hiking enthusiasts will enjoy climbing the Camden Hills-a quick 45 minute drive from the lake. You’ll love my place because of the views, the ambiance, the people, and the location. My place is good for couples and solo adventurers.

Superhost
A comfortable room features a full size bed with a floral quilt. In one corner, a reading chair displays a colorful striped pattern. A desk with a lamp is positioned nearby, alongside a dresser equipped with a coffee maker and other amenities. Natural light filters through a window adorned with curtains.
Guest suite in Hallowell
4.84 out of 5 average rating, 227 reviews

Room B with private entrance, bathroom & hot tub

Room B is a small (10’ x 10’) but cozy room with full size bed with luxury mattress and private bathroom (5’ x8’) with towel warmer & glass shower. The room includes a desk, TV, minifridge, microwave, coffee maker, dresser, reading chair & private entrance. In the summer we have bicycles to use on the rail trail and kayaks for the Kennebec River. Year round hot tub. Downtown is just a block away where there are numerous restaurants and pubs with live music. Hiking trails & waterfalls nearby.

Top guest favourite
Guest suite in Monmouth
4.97 out of 5 average rating, 198 reviews

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.

Guest favourite
An open living area showcases a modern design with wooden beams across the ceiling. A comfortable chair and a coffee table are positioned on a patterned rug, while a kitchen with blue cabinetry is visible in the background, featuring stainless steel appliances and ample natural light from windows.
Apartment in Richmond
4.9 out of 5 average rating, 245 reviews

Designers Dream 1br Apt where class meets relax!!!

This Designers Dream 1br apartment is located in the quintessential small Maine town of Richmond. Open the door feast your eyes on this truly unique and beautiful spot and get ready to relax or explore! Richmond is home of Swan Island a great spot to explore via kayak or canoe or just grab the ferry! We're 45 min to all downtown Portland has to offer. We are an hour to Booth Bay Harbor and the beautiful botanical gardens. Popham beach is 45 min away, one of the most amazing beaches in state.

Guest favourite
Cottage in Sabattus
4.95 out of 5 average rating, 138 reviews

Maine lakehouse-Ice fishing, skiing, snowmobiling

Beautiful lake living & winter activities, 2.5 hours from Boston, 40 min. from Portland. Near skiing- 1:20 from Sunday River, 1:10 Pleasant Mtn., 1:05 Mount Abram Ski Area, 0:20 Lost Valley. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances. Minutes to Lewiston/Auburn - close to dining and stores. Well known ice fishing spot , cross-country skiing nearby too. Fire pit, great sunsets.

Top guest favourite
An open living space features a cozy seating area with a light-colored sofa and a decorative area rug. A spacious bed is placed in one corner, accompanied by soft bedding. The kitchenette is visible in the background, along with a doorway leading to a bathroom.
Apartment in Gardiner
4.98 out of 5 average rating, 167 reviews

The Escape on Elm

Our charming Airbnb is located in the heart of Gardiner Maine. Built in 1850, our historic home combines old-world charm with modern comforts. Enjoy the creaking hardwood floors, exposed beams, and coastal accents that create a calming, seaside vibe. The open layout offers a spacious living room with a sofa bed, Smart TV, books and board games. We offer a comfortable sleeping area with a queen bed. A full bathroom. Enjoy cooking in the fully equipped kitchen that opens to a private porch.

Top guest favourite
The studio apartment features warm wood flooring and a bright, airy atmosphere. A spacious bed with patterned bedding is visible, along with a dining table and chairs. A kitchenette area is equipped with appliances, and artwork adorns the walls, adding character to the room.
Guest suite in Hallowell
4.99 out of 5 average rating, 103 reviews

Welcome to the Brown House! Hallowell studio

Enjoy Hallowell and Central Maine while staying at our studio apartment. An easy walk to downtown Hallowell to shops, restaurants , and pubs. Take a walk on the Kennebec Rail Trail . A 15 minute drive to visit Maine Cabin Masters. Hour drive to Boothbay Harbor, Rockland, or Belfast. Studio is located above owners garage : separate entrance and off street parking. Included: linens, towels, TV, WiFi, single Keurig, microwave, toaster, college size dorm fridge, small cooler

Top guest favourite
A spacious living area is presented, featuring a light wood dining table with chairs, a comfortable sofa, and a workspace with a desk and chair. Large windows offer views of the surrounding fields, while a kitchen with modern appliances is visible in the background.
Apartment in Palermo
4.98 out of 5 average rating, 108 reviews

One bedroom apartment in rural Waldo County, Maine

A peaceful and scenic setting amidst hay fields in Palermo, ME, a rural location in Waldo County. Central and Mid-coast Maine travel distances (mi.): Waterville: 20; Rockland: 34; Augusta: 24; Belfast:26. The building's lower apartment is dedicated to Airbnb guests. Notes: Smoking is not permitted anywhere on the premises! Evening restaurant options are available only in the locations listed above. There are six entrance steps. Please provide advance notice regarding pet(s)!

Top guest favourite
Loft in West Gardiner
4.96 out of 5 average rating, 224 reviews

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 newly renovated studio apartment is furnished with a spacious bed, a black sofa, and a small dining table. Modern kitchen appliances, including a refrigerator and stove, are visible. Natural light fills the room through a window, complemented by soft lighting from table lamps.
Apartment in Augusta
4.9 out of 5 average rating, 101 reviews

Downtown Augusta Studio - Newly Renovated #3

Located at the heart of downtown Augusta, this newly renovated studio apartment is a wonderful choice when visiting Augusta Maine! The 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 parking and free laundry available on site. Enjoy a stylish experience at this centrally-located place.

Top guest favourite
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
4.98 out of 5 average rating, 86 reviews

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.

Top guest favourite
A bright, inviting living space features large windows overlooking the serene woods and lake. Two rocking chairs and a coffee table are centered on a woven rug, while a cozy wooden table is positioned nearby, creating a peaceful atmosphere.
Cabin in Winthrop
4.98 out of 5 average rating, 56 reviews

Lake Cabin in the Trees

Quiet lakefront cabin tucked in the woods with shimmering views of Wilson Pond below, the last house on a private dirt road. Dive in for a swim from the private dock or kayak to the lake's small islands. Stay connected with a dedicated office with desk and fast internet. A calm, secluded getaway for any season.

Popular amenities for Winthrop vacation rentals

When is the best time to visit Winthrop?

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Avg. price$226 CAD$246 CAD$250 CAD$250 CAD$321 CAD$323 CAD$328 CAD$342 CAD$308 CAD$304 CAD$274 CAD$279 CAD
Avg. temp-6 °C-5 °C0 °C6 °C12 °C17 °C21 °C20 °C16 °C9 °C3 °C-2 °C

Frequently Asked Questions

  • What are the most popular amenities for Cabin Rentals in Winthrop?

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do cabin rentals in Winthrop have air conditioning?

    Absolutely! We offer over 10 cabin rentals with air conditioning in Winthrop. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winthrop have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Winthrop. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Winthrop?

    Four-legged friends are welcome in Winthrop. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Winthrop?

    Yes! Work meets play with ease at over 30 vacation rentals in Winthrop featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Winthrop have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Winthrop. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Winthrop?

    Winthrop has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cabin rentals in Winthrop?

    Experience the best of Winthrop with our cabin rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Quick stats about vacation rentals in Winthrop

  • Total vacation rentals

    Explore 70 vacation rentals in Winthrop

  • Nightly prices starting at

    Winthrop vacation rentals start at $55 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,170 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Winthrop vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Winthrop rentals

  • 4.9 Average rating

    Winthrop stays are highly rated by guests—averaging 4.9 out of 5!

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