Vacation rentals in Winslow

Find and book unique accommodations on Airbnb

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.

1 of 1 pages1 / 1
Top guest favorite
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
4.99 out of 5 average rating, 136 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.

FamilyValueCheck-in

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, 40 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.

FamilyLocationParking

Top guest favorite
Condo in Oakland
5.0 out of 5 average rating, 111 reviews

Home away from home cozy new Apartment in Oakland

Escape to this newly built apartment in Oakland for a relaxing and peaceful getaway. Unwind on the porch while enjoying Maine’s beautiful wildlife, breathtaking sunsets, and star-filled skies. Conveniently located just minutes from Colby College, Thomas College, Snow Pond public beach/boat landing, Bowl in the Pines, and many local restaurants, shops, and outdoor attractions. Perfect for a vacation exploring beautiful Central Maine, visiting family, college visits, or business travel.

LocationFamilyCondition

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 .

LocationValueIndoor spaces

Superhost
Apartment in Winslow
5.0 out of 5 average rating, 7 reviews

Entire 3 BR apartment in Winslow| 2nd FL | 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

FamilyLocationLaundry

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.

FamilyValueCheckout

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, 54 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.

LocationFamilyDecor

Top guest favorite
An open living area features a cozy seating arrangement next to an elegant stone fireplace. A circular coffee table sits on a textured area rug, and large windows provide ample natural light. A kitchen island with bar stools is visible, allowing for casual dining.
Home in Oakland
4.98 out of 5 average rating, 45 reviews

Ultra Spacious and Hosts are Gracious

Enjoy easy access to everything from this centrally located 3 bedroom/2.5 bath home. Newly renovated, very spacious sunlit home only 2 miles from I-95, public beach 1 mile, Colby College 6 miles, Thomas College 3 miles, Waterville 3 miles, Augusta 15 miles, and in the heart of the Belgrade Lakes chain. Many food options in all directions. Clean, comfortable, open, bright, and includes a private yard. This home sleeps up to 6 guests with its 3 queen beds.

FamilyLocationLayout

Top 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.

FamilyValueAmenities

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, 127 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.

LocationFamilyCondition

Guest favorite
Apartment in Waterville
4.92 out of 5 average rating, 65 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.

ValueFamilyParking

Guest favorite
Home in Oakland
4.95 out of 5 average rating, 84 reviews

Classy AF Home, walk across the street to Colby!

THE BOOKING CALENDAR OPENS ONE YEAR IN ADVANCE, INCLUDING GRAD WEEKEND. Lovingly renovated three bedroom home across the street from Colby College’s Senior Drive. My grandfather built our house in the 40’s, we have done all of the renovations ourselves to create open, inviting spaces with unique touches while maintaining the original footprint. Our home is a labor of love that we hope YOU love. *Pets ok w/ notice and 50$ fee*

FamilyLocationPool

Popular amenities for Winslow vacation rentals

When is the best time to visit Winslow?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$12,131 GYDG$23,426 GYDG$24,053 GYDG$26,145 GYDG$25,099 GYDG$27,609 GYDG$16,314 GYDG$14,641 GYDG$11,504 GYDG$10,040 GYDG$6,275 GYDG$17,360 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 apartment rentals in Winslow have air conditioning?

    Absolutely! We offer over 30 apartment 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 30 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 30 apartment 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.