Vacation rentals in Winslow

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Top-rated vacation rentals in Winslow

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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 out of 5 average rating, 30 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 modern A-Frame cabin is nestled among vibrant trees, featuring large glass windows that illuminate the interior with a warm glow. A welcoming deck extends from the entrance, inviting guests to enjoy the surrounding forest ambiance.
Cabin in Chesterville
4.99 out of 5 average rating, 189 reviews

Off-Grid Escape. Wood Fired Hot Tub. 4 Kayaks

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

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 favorite
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 favorite
The kitchen features granite countertops and a combination of white cabinetry. Large windows provide natural light, illuminating the spacious area. Appliances include a stainless steel refrigerator and stove, while ample counter space allows for cooking and meal preparation.
Apartment in Waterville
5 out of 5 average rating, 20 reviews

Downtown Waterville Apartment

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!

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, 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 .

Top guest favorite
A spacious living area is presented, featuring a light wood dining table with chairs, a comfortable sofa, and a workspace with a desk and chair. Large windows offer views of the surrounding fields, while a kitchen with modern appliances is visible in the background.
Apartment in Palermo
4.98 out of 5 average rating, 108 reviews

One bedroom apartment in rural Waldo County, Maine

A peaceful and scenic setting amidst hay fields in Palermo, ME, a rural location in Waldo County. Central and Mid-coast Maine travel distances (mi.): Waterville: 20; Rockland: 34; Augusta: 24; Belfast:26. The building's lower apartment is dedicated to Airbnb guests. Notes: Smoking is not permitted anywhere on the premises! Evening restaurant options are available only in the locations listed above. There are six entrance steps. Please provide advance notice regarding pet(s)!

Top guest favorite
An open-concept great room features high wooden ceilings with exposed beams. Large windows provide ample natural light and views of the surroundings. A comfortable seating area includes a sofa and coffee table, while a dining space with chairs is positioned near the kitchen.
Cottage in South Thomaston
4.96 out of 5 average rating, 202 reviews

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

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, 163 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 out of 5 average rating, 107 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.

Top guest favorite
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, 363 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.

Top guest favorite
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
4.99 out of 5 average rating, 252 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.

Popular amenities for Winslow vacation rentals

When is the best time to visit Winslow?

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Avg. price$58$112$115$70$80$108$78$70$55$48$30$83
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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 vacation rentals in Winslow

  • Total vacation rentals

    Explore 70 vacation rentals in Winslow

  • Nightly prices starting at

    Winslow vacation rentals start at $10 per night before taxes and fees

  • Verified guest reviews

    Over 1,770 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 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

  • 4.6 Average rating

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

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