Holiday houses in Winslow

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Top-rated holiday rentals in Winslow

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Top Guest favourite
A dining area is presented with a large wooden table, surrounded by metal chairs. Natural light enters through a nearby window, illuminating the space. A decorative bowl filled with flowers sits at the center of the table, enhancing the inviting atmosphere. Simple wall art complements the decor.
Apartment in Waterville
5 out of 5 average rating, 135 reviews

Sweet Retreat: 3 BDR Stylish Home Mins To Colby

Stay in the heart of Maine - Vacationland! This spacious 1,200 sq. ft. ground-floor home is just 1.1 miles from I-95, making it an ideal base for exploring our beautiful state. We're about 1 hour from Portland and 1.5 hours from Bar Harbor & Acadia National Park. Enjoy the perfect blend of modern comfort and rustic charm in this inviting two-family home. As a bonus, guests have access to a private backyard featuring a patio set, fire pit, garden, fenced area, and mature trees for added privacy.

Top Guest favourite
The entrance to the apartment features a red door framed by two white columns. A small planter with pink flowers sits beside the door. The porch has a wooden floor and is partially covered, offering shelter from the elements.
Apartment in Waterville
5 out of 5 average rating, 34 reviews

Clean & Comfortable, 2nd Fl Apt

Waterville is a small town just off the interstate in Central Maine and is approximately an hour from all major cities, the mountains, the coast, and about 2 1/2+-hrs to Acadia. The rental is in a residential neighborhood less than a mile from the interstate, Colby, restaurants, shopping, movies, and parks. There are many recreational opportunities nearby to walk/run, hike, bike, and/or kayak. The apartment has a private entrance, on the second floor (13 stairs up) in an owner occupied duplex.

Superhost
This tiny home on wheels showcases a modern exterior with large windows and a sleek black design. A small set of steps leads to the entrance, while a green mat is placed at the door. Lush greenery surrounds the home, enhancing its natural setting.
Tiny home in Winslow
4.63 out of 5 average rating, 24 reviews

Tiny home on wheels

Experience the charm of camping right in the front yard with this one-of-a-kind tiny home on wheels! Recently built, it features high ceilings, a full-size kitchen, a spacious shower, washer and dryer, a king-size bed, a full-size pullout sofa, and a dining table giving you the comfort and feel of a much larger home. Stay cool with summer AC or unwind by the outdoor fireplace for a cozy evening. Spend your days exploring endless recreational activities, China Lake is just 3 minutes away.

Guest favourite
A spacious living room features a large sectional sofa adorned with colorful cushions. A decorative area rug rests on hardwood flooring, complementing the light walls and artwork. A lamp emits soft light beside the sofa, while a potted plant adds a touch of greenery.
Home in Waterville
4.87 out of 5 average rating, 232 reviews

Cozy House in Waterville

Our private Cozy House has just been renovated! We put in a new kitchen, bathroom, laundry room, and a big 4k smart tv/Apple TV. It's in a friendly neighborhood located in the heart of Waterville only five minutes from Colby College, Thomas College (by car) and just a few minutes from downtown Waterville. Everything is very close to our location. There's a Hannafords nearby, Maine General Hospital and many restaurants, schools and stores. We are located on a private dead-end driveway .

Guest favourite
A serene outdoor area is framed by lush greenery and trees, showcasing vibrant orange flowers in the foreground. A meandering stone path leads towards a gathering area in the distance, partially visible through the foliage.
Home in Sidney
4.87 out of 5 average rating, 112 reviews

Brook Ridge Retreat

Work, play, & relax at Brook Ridge Retreat! Come visit your Colby or Thomas College student and have the comforts of home. Do some grilling or cook up a favorite meal in the full kitchen. Remotely connect to work or school at our custom-made desk and dedicated office area with wireless printer and available computer monitor. Splash in the brook or in the basin, and sit under the waterfalls. WiFi, firepit, Keurig or french press, electric fireplace, large decks, & big yard.

Top Guest favourite
An outdoor dining area is featured with a sturdy table and chairs, shaded by a large umbrella. A grill is positioned nearby, with an expansive view of lush green hills and a clear blue sky stretching into the distance.
Home in Freedom
4.98 out of 5 average rating, 43 reviews

Halcyon Ridge

Halcyon Ridge is owned by Lynn & Chuck Hadyniak, who live nearby. Lynn & Chuck moved out of New Jersey years ago to get away from the hustle & bustle, & raise a family in peace. They love Freedom for its quiet & natural beauty, & would love to host people at Halcyon Ridge who also want to escape the noise. Stargazers will be delighted: low humidity, expansive view of the southeastern sky, & next to no light pollution, make for wonderful viewing. Rest. Relax. Recharge.

Top Guest favourite
A cozy bedroom features a king-sized bed with a textured blue coverlet and accent pillows. Two windows provide natural light, while decorative lamps sit atop the bed's headboard. A fan is positioned nearby, and a vibrant orange door adds a pop of color.
Home in Brooks
4.98 out of 5 average rating, 145 reviews

Secluded Retreat w/ Luxe Hot Tub & Forest Views

Tucked near the woods of Maine, this peaceful cabin offers the perfect escape. Soak in the private hot tub under the stars, curl up by the electric woodstove, or work remotely with fast Wi-Fi and forest views. The cabin features a comfy king bed, full kitchen, clean modern bath, and self check-in. Enjoy your morning coffee in the sunroom or take a short drive to explore Belfast and the coast. Quiet, cozy, and surrounded by nature—ideal for rest, romance, or reflection.

Top Guest favourite
A corner of the enclosed front porch showcases a wicker chair adorned with a colorful throw blanket. A small, coral-colored table holds a coffee cup, while a potted plant adds a touch of greenery. Natural light streams through the large windows.
Home in Waterville
4.9 out of 5 average rating, 167 reviews

Sterling House

1960’s Cape in a quiet, centrally located neighborhood. We are licensed with the City of Waterville as a STR. Sleeps (7) comfortably. Less than two miles to Waterville’s Downtown area with several restaurants and bars, Waterville Opera House, Colby College, Thomas College as well as MaineGeneral Thayer Hospital. We are a pet-free home with NO central A/C - fans only. Landscaping: We have a lawn service every other Wednesday between 7:30am and 9am.

Guest favourite
Apartment in Waterville
4.92 out of 5 average rating, 63 reviews

Sun-kissed Serenity - 2 Bdrm Apt with Sunroom

This second floor apartment is conveniently located in central Waterville. Designed for long or short stays, it has a fully equipped kitchen, cozy living spaces, and comfortable bedrooms. Take advantage of our amenities, including high-speed internet and on-site laundry! This apartment also features a private 3-season sunroom with an electric fireplace. Take time to relax in this space and experience the different seasons Maine has to offer.

Top Guest favourite
A contemporary yurt is nestled among snow-dusted trees, surrounded by a blanket of white snow. A spacious deck extends from the yurt, providing access to the inviting living space. The serene winter landscape and trees enhance the retreat's secluded charm.
Yurt in Appleton
4.95 out of 5 average rating, 372 reviews

SNOW SWEET, A Yurt for All Seasons

Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Guest favourite
A spacious two-story home is showcased amidst a snowy landscape. Snow covers the roof and ground, while evergreen trees flank the entrance. Festive decorations accent the front door, and a gentle snowfall creates a serene atmosphere on the property.
Guest suite in Oakland
4.98 out of 5 average rating, 259 reviews

Cozy Studio Flat, Belgrade Lakes Region

Kick back and relax in this calm, stylish, newly renovated second floor space over the garage. Enjoy four seasons in the Belgrade Lakes region of Central Maine. Hunting, fishing, hiking, biking, skiing, and snowmobiling, to name a few of the many activities available. We are 2 miles from Oakland Waterfront Park on Messalonskee Lake and just over an hour drive from both beaches and ski resorts.

Top Guest favourite
Condo in Oakland
5 out of 5 average rating, 97 reviews

Home away from home cozy new Apartment in Oakland

Have a relaxing and peaceful getaway in this newly built apartment in Oakland. It’s conveniently located within minutes to Colby College, Thomas College, Maine General, Northern Lights, Snow Pond public beach and boat landing.

Popular amenities for Winslow holiday rentals

When is the best time to visit Winslow?

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Avg. price$83 AUD$160 AUD$164 AUD$100 AUD$114 AUD$154 AUD$111 AUD$100 AUD$79 AUD$69 AUD$43 AUD$119 AUD
Avg. temp-7°C-6°C-1°C6°C13°C18°C21°C20°C16°C9°C3°C-3°C

Frequently Asked Questions

  • Are there family-friendly apartment rentals in Winslow?

    Winslow has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Winslow?

    Experience the best of Winslow with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Winslow?

    Four-legged friends are welcome in Winslow. Choose from more than 10 vacation rentals for guests traveling with pets.

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

    Yes! Work meets play with ease at over 20 vacation rentals in Winslow featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Winslow have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Winslow. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Winslow have a kitchen?

    Absolutely! We offer over 20 apartment rentals with a kitchen in Winslow. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Winslow have wifi?

    Absolutely! We offer over 20 apartment rentals with wifi in Winslow. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Winslow have free parking?

    Absolutely! We offer over 20 apartment rentals with free parking in Winslow. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Winslow

  • Total holiday rentals

    Explore 70 holiday rentals in Winslow

  • Nightly prices starting at

    Winslow holiday rentals start at $14 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,770 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Winslow holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winslow rentals

  • 4.6 Average rating

    Winslow stays receive an average rating of 4.6 out of 5 from guests

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