
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.

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.

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.

epicurean feast with zen like surroundings
My sister and i will welcome you to our guest cottage on a quiet lake in Belgrade. We are including a dropped off gourmet breakfast-you pick the time, between 7:30 and 9:00. We include waterfront access as well as use of a kayak. We are located on a beautiful lake in the middle of the woods. Peaceful and absolulely quiet. We will practice extreme sanitation as well as social distancing. One well behaved dog is welcome as long as they are not left alone in the cottage- dog bed supplied.

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 .

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

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.

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.

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.

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.

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.

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.

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
Stay near Winslow's top sights
Other great vacation rentals in Winslow

Charming Private camp on China Lake

Classy AF Home, walk across the street to Colby!

The heart of the Belgrade lakes

2 Bedroom Apartment

Cozy Maine Cabin With Lake Views (No Water Access)

Waterfront.Get away from it all.

Cozy Uptown Waterville

Newly Constructed Apartment — 7 Min to Colby
When is the best time to visit Winslow?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$12,131 GYD | G$23,425 GYD | G$24,053 GYD | G$26,145 GYD | G$25,099 GYD | G$27,609 GYD | G$16,314 GYD | G$14,641 GYD | G$11,504 GYD | G$10,039 GYD | G$6,275 GYD | G$17,360 GYD |
| 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 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.
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- Pemaquid Beach
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- Coastal Maine Botanical Gardens
- The Camden Snow Bowl
- Maine Maritime Museum
- Rockland Breakwater Light
- Farnsworth Art Museum
- Camden Hills State Park
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- Belgrade Lakes Golf Club
- Lost Valley Ski Area
- Range Ponds State Park
- Sugarloaf Golf Club





