
Holiday houses in Winslow
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Quick stats about holiday rentals in Winslow

Total holiday rentals
Explore 80 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 1,940 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 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

4.7 Average rating
Winslow stays receive an average rating of 4.7 out of 5 from guests
Top-rated holiday rentals in Winslow
Guests agree: these stays are highly rated for location, cleanliness and more.

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.
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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.
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Sister a-frame in Woods (B)
Escape to one of our two sister A frames. These cozy cottages are nestled in the Oakland, Maine woods. Close proximity to I-95, Messalonskee and prestigious Belgrade Lakes you will find home to a wide variety of wildlife and nature. Boating, fishing and ATV riding close by! The campus includes a loft with a view, walking trail, free/overflow parking. A luxury, campy feel makes this a perfect getaway for you and your family. Check out our other listings managed by Hall’s Homes RE online!
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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.
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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 .
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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
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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.
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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.
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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.
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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.
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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.
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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*
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Popular amenities for Winslow holiday rentals
Stay near Winslow's top sights
Other great holiday rentals in Winslow

Charming Private camp on China Lake
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Beautiful Lakefront Cottage China Lake Maine
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Ultra Spacious and Hosts are Gracious
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Minutes to Colby/ Main Street
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Camp Giguere On China Lake- Sleeps 8- Sunset views
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Cozy Maine Cabin With Lake Views (No Water Access)
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Cozy apartment -Waterville Maine
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Cozy Uptown Waterville
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When is the best time to visit Winslow?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $82 AUD | $158 AUD | $162 AUD | $177 AUD | $169 AUD | $186 AUD | $110 AUD | $99 AUD | $78 AUD | $68 AUD | $42 AUD | $117 AUD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 13°C | 18°C | 21°C | 20°C | 16°C | 9°C | 3°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.
Destinations to explore
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- The Camden Snow Bowl
- Maine Maritime Museum
- Rockland Breakwater Light
- Farnsworth Art Museum
- Camden Hills State Park
- Cellardoor Winery
- Maine Lighthouse Museum
- Moose Point State Park
- Hollywood Slots Hotel & Raceway
- Black Mountain of Maine
- Belgrade Lakes Golf Club
- Range Ponds State Park
- Lost Valley Ski Area
- Sugarloaf Golf Club





