Vacation rentals in Winthrop

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winthrop

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

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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, 246 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.

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 open-concept living area features a comfortable couch and a recliner, complemented by a dining table and modern kitchen appliances. Natural light enters through the windows, illuminating the space that is adorned with neutral tones and wood flooring.
Cottage in Augusta
5 out of 5 average rating, 112 reviews

Modern Hideaway in Augusta

Centrally located modern guest home in Augusta, access points to Portland, Midcoast Maine, and Bangor. Spacious master bedroom with closet, additional bedroom, both bedrooms with queen size beds. Handicap bathroom equipped with grab rail and also handicap accessible shower with sit down bench. Many brand new amenities. 55 inch TV has Roku with access to Netflix , Disney Plus, and more! Strong WiFi with the ability to work remotely if needed and explore Augusta and surrounding area.

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 wooden porch is adorned with rustic log walls and soft lighting from string lights overhead. Comfortable seating, including wicker chairs and a green bench, creates a cozy space for relaxation, surrounded by lush greenery visible through the windows.
Cabin in Georgetown
4.88 out of 5 average rating, 144 reviews

Cozy log cabin on private pond, near Reid St Park!

Winter or summer, the Little River Retreat will help you step away from the world - but still be minutes from Reid State Park, Five Islands Lobster, the Georgetown General Store, and the rugged beauty of Midcoast Maine. This is our family camp, with our own books, games, and “vibe”. It is not a hotel, and some things may not be “industry standard”. We love the unique charm of this space and place, and many repeat guests do too. We hope you will treasure (and care for it) as we do!

Top guest favourite
The exterior of a Victorian farmhouse is showcased, featuring classic white siding and multiple large windows. Lush green trees frame the house, while vibrant pink and purple flowers add color to the front yard. A covered porch invites relaxation.
Apartment in Lisbon falls
4.94 out of 5 average rating, 515 reviews

Charming Victorian farmhouse 1880's bedrooms-2

Victorian farmhouse 1880's Stay in an "era gone by". Private 2 bedroom. Original hardwood floors. Original pocket doors. Sleeps 6. Has living room, kitchen, dinning area 1 bathroom with tub , study area. Charming town, population 4000+. smoke free house. Private keyless entry. The blue door. Free wifi, cable, roku. Has keurig coffee maker with free coffee, dishes, pots, pans, silverware, nu-wave cooktop, toaster, microwave, fridge, pack n play. Queen beds. W & D private.

Top guest favourite
Loft in West Gardiner
4.96 out of 5 average rating, 225 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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