Holiday houses in Winthrop

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Top-rated holiday rentals in Winthrop

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

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Top Guest favourite
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
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.

Top Guest favourite
A bright eat-in kitchen area features a small wooden table with two chairs. Natural light streams through large windows, providing a view of the lush garden. A washer and dryer are positioned nearby, enhancing the functionality of the space.
Apartment in Bath
4.96 out of 5 average rating, 161 reviews

1820s Maine Cottage with Garden

Enjoy a cozy shipbuilder's cottage in Bath, Maine. This quaint apartment attached to a family home has its own entrance and contains a bedroom, a bathroom, a kitchen, and a living room with antique details that reflect its 200-year old history. Only a 15-minute walk to historic downtown Bath, a 3-minute drive to Thorne Head Preserve, and a 25-minute drive to Reid State Park and Popham Beach. Come appreciate everything MidCoast Maine has to offer! PLEASE NOTE: This apartment has steep stairs!

Guest favourite
A cabin with a wooden exterior is set amidst a forest, surrounded by trees. A gravel pathway leads to the entrance, and a metal staircase provides access to the porch. The structure features large windows and a green metal roof.
Cabin in Litchfield
4.98 out of 5 average rating, 60 reviews

Cozy Cabin with Lake Access

This cozy cabin includes access to Lake Cobbossee, one of the most popular lakes in central Maine. It’s tucked away in a small private community where you can escape into peace and relaxation. The cabin is newly renovated and the yard is surrounded by trees, leaving you with plenty of privacy to roast s’mores and have cookouts with your family. It’s a short walk to the lake where you can drop in your kayak or throw a line out to one of the best fishing/recreational lakes in central Maine.

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, 102 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

Guest favourite
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
4.81 out of 5 average rating, 136 reviews

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.

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, 510 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
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
4.97 out of 5 average rating, 195 reviews

Hallowell Hilltop Home with 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, 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.

Guest favourite
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
4.96 out of 5 average rating, 220 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.

Top Guest favourite
A bright living area features modern furnishings and natural light streaming through two large windows. A cozy seating arrangement includes a minimalist sofa and an accent chair. A wooden media console holds a flat-screen TV, while a round yellow rug adds a lively touch to the space.
Apartment in Hallowell
4.98 out of 5 average rating, 401 reviews

Two Bedroom Mid Century Modern Downtown Apartment

Experience this amazing two bedroom Mid-Century Modern apartment in Downtown Hallowell. This is newly renovated & steps away from a variety of restaurants & pubs. It has all the fun and funky charm of the early 1960’s with bright colors, rich woods, clean lines & shag rugs. All the modern comforts including stainless steel appliances, vessel sinks, soaker tub & new beds. A couple miles from the State Capital and centrally located between Brunswick and Waterville.

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 holiday rentals

When is the best time to visit Winthrop?

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Avg. price$272 NZD$297 NZD$302 NZD$302 NZD$388 NZD$389 NZD$396 NZD$412 NZD$371 NZD$412 NZD$328 NZD$297 NZD
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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 holiday rentals in Winthrop

  • Total holiday rentals

    Explore 70 holiday rentals in Winthrop

  • Nightly prices starting at

    Winthrop holiday rentals start at $66 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,170 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Winthrop holiday rentals include Wi-Fi 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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