Holiday houses in Winslow

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Top-rated holiday rentals in Winslow

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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, 32 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
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
4.84 out of 5 average rating, 58 reviews

Entire 3 BR apartment in Winslow

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. 10 mins drive to Colby college due to bridge closure 3 mins drive to Downtown Waterville 2 mins drive to restaurant in downtown Winslow 25 minutes drive to Augusta, ME

Guest favourite
A two-story house showcases a charming design with a gray exterior and red front doors. Green trees frame the property, providing a natural backdrop. The inviting driveway leads to the entrance, with windows allowing for ample natural light.
Home in Oakland
4.93 out of 5 average rating, 147 reviews

Updated 4br Family Home Near Belgrade Lakes

Stay at our Maine Getaway. Our fully renovated 1940s New Englander is sure to bring you peaceful vibes and luxury. Come play Pickleball with just a quick walk over to the courts, driving not necessary!Close to downtown Waterville, Colby College, Thomas College, UMaine Farmington. 2 min from Messalonskee Lake boat launch where you can boat, kayak, canoe, & ice fish. Proximity to ski mountains, Titcomb, Black Mountain, Sugar Loaf & Sunday River. Please note BBQ is only accessible May-October.

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
4.86 out of 5 average rating, 228 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, 42 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
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 438 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

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

Downtown Waterville 2 Bedroom

Experience the charm and convenience of this second 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, a formal dining room, cozy living room, and 2 bedrooms. Stunning city views, making this the perfect retreat. Easy check-in & check-out!

Top Guest favourite
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, 189 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.

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, 165 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 favourite
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 out of 5 average rating, 110 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 favourite
A spacious living area is featured with hardwood flooring and a comfortable seating arrangement. A smart TV is prominently displayed on a dark wooden console. Soft yellow flowers in a vase add a touch of warmth. A glimpse of a cozy bedroom is visible through the open doorway.
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.

Popular amenities for Winslow holiday rentals

When is the best time to visit Winslow?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$99 NZD$191 NZD$196 NZD$119 NZD$136 NZD$184 NZD$133 NZD$119 NZD$94 NZD$82 NZD$51 NZD$142 NZD
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 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 apartment rentals in Winslow have air conditioning?

    Absolutely! We offer over 20 apartment 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 house rentals in Winslow have wifi?

    Absolutely! We offer over 40 house rentals with wifi in Winslow. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winslow have free parking?

    Absolutely! We offer over 30 house 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 $17 NZD 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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