Vacation rentals in Winslow

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Quick stats about vacation rentals in Winslow

  • Total vacation rentals

    Explore 80 vacation rentals in Winslow

  • Nightly prices starting at

    Winslow vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,940 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Winslow vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winslow rentals

  • 4.7 Average rating

    Winslow stays receive an average rating of 4.7 out of 5 from guests

Top-rated vacation rentals in Winslow

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

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Top guest favorite
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
5.0 out of 5 average rating, 39 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.

Top guest favorite
The open-concept living area showcases natural wood walls and a ceiling, with large windows allowing ample light. A soft sofa and a daybed are arranged around a round coffee table on a striped area rug. A staircase leads to the upper level, visible in the background.
Home in Farmington
4.97 out of 5 average rating, 323 reviews

Carriage House

Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.

Guest favorite
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
4.86 out of 5 average rating, 235 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 .

Superhost
Apartment in Waterville
5.0 out of 5 average rating, 3 reviews

Loft on Common

Experience the charm and convenience of this top floor apartment, perfectly situated in the heart of the city's vibrant downtown. Within walking distance to local shops, restaurants, and opera house, you'll be immersed in all that Waterville has to offer. Inside, you'll feel right at home with a fully equipped kitchen, hardwood floors, a formal dining room, cozy living room, and a luxurious king-sized bed. Stunning city views, making this the perfect retreat. Easy check-in & check-out!

Superhost
A light-colored sectional sofa is positioned on a soft area rug, complemented by decorative pillows. A dark wood coffee table with storage compartments sits in front. Sheer, pattern curtains frame the windows, while a potted plant adds a touch of greenery to the space.
Apartment in Winslow
4.86 out of 5 average rating, 65 reviews

1st FL | Entire 3 BR apartment in Winslow| 3 BR

Welcome to our stylish three bedroom apartment, recently renovated, nestled on a quiet street near high school. This inviting space has a separate entrance. The apartment is furnished with a comfortable queen sized bed, wifi, a work area, and a washer/dryer to maximize comfort and functionality. Free Parking on the driveway. 5 mins drive to Colby college due 3 mins drive to Downtown Waterville 2 mins drive to restaurant in downtown Winslow 25 minutes drive to Augusta, ME

Top guest favorite
Cabin in Liberty
4.94 out of 5 average rating, 47 reviews

Modern Cabin on Crie Hill

Unwind at this secluded hillside hideaway. Perched above the valley with sweeping ridge views, this newly built cabin blends comfort with privacy. Begin your day soaking in the outdoor tub as morning mist drifts up from the valley below, or gather around the granite fire pit in the evening while grilling under the open sky. Designed with sustainability in mind, the retreat runs on solar power backed by a quiet propane generator to ensure a worry-free stay even on cloudy days.

Guest favorite
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
4.86 out of 5 average rating, 117 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 favorite
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, 53 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 favorite
A modern kitchen space features metal shelving with glassware and utensils. A stainless steel table holds bowls and a vase of hydrangeas. A door leads to a closet, and a silver trash can is positioned nearby. Artwork is displayed on the wall, adding a touch of character.
Apartment in Waterville
4.98 out of 5 average rating, 190 reviews

Sweet Retreat: 2 BDR Home Mins to Colby

Minutes from from Colby College (1.5 miles) , Inland Hospital (1 mile), Maine General (2 miles), Exit 127 on I-95 (5 miles). Forced air heat, WiFi, TV (Hulu & Netflix).The apartment is in a quiet, family friendly Waterville neighborhood on the second story of a two family home- has a private entrance, parking, two bedrooms (queen beds), one bathroom (full bath), dining area, fully equipped kitchen ( stove, oven, microwave), Screened in porch and patio.

Guest favorite
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, 173 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.

Top guest favorite
The cabin is viewed from the water, framed by lush greenery and tall trees. A spacious porch extends across the front, highlighting the cabin's inviting structure, while the calm water reflects the surrounding nature and the bright exterior of the building.
Cabin in Augusta
5.0 out of 5 average rating, 125 reviews

Price's Point - Cabin on the water

Brand new Cozy Cabin on a small 181 acre pond. Enjoy the cabin feel of knotty pine and a big country porch overlooking the water. Walk in access to the water or ice in the winter. Kayaking, canoeing, ice fishing, snowmobiling and more depending on the time of year. A peaceful location a mile down a private road but 10 minutes away from a grocery store etc. Eagles, loons and fish will be your neighbors as you are in the moment at Price's Point.

Guest favorite
Apartment in Waterville
4.92 out of 5 average rating, 64 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.

Popular amenities for Winslow vacation rentals

When is the best time to visit Winslow?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$12,136 GYDG$23,434 GYDG$24,062 GYDG$26,154 GYDG$25,108 GYDG$27,619 GYDG$16,320 GYDG$14,646 GYDG$11,508 GYDG$10,043 GYDG$6,277 GYDG$17,366 GYD
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 vacation rentals in Winslow?

    Winslow has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Winslow with our house rentals, starting at about $10 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 20 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 house rentals in Winslow have a kitchen?

    Absolutely! We offer over 30 house 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 30 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.