
Holiday rentals 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 €9 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
70 of Winslow holiday rentals include wifi 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.

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.

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 .

Super cute waterfront cottage
Beautiful four-season waterfront cottage located on the outskirts of Augusta. The main living space has a full kitchen, living room/dining space, bathroom with laundry, and bedroom (queen bed). The walk-out basement, with its own bathroom, offers a cabin-style space to lounge in or as a second bedroom. Or stay outside and enjoy the water views from the second-story deck or ground-level fire pit. Either spot is an amazing place to enjoy the night sky and listen to the loons and eagles!

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.

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.

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.

Home away from home cozy new Apartment in Oakland
Have a relaxing and peaceful getaway in this newly built apartment in Oakland. It’s conveniently located within minutes to Colby College, Thomas College, Maine General, Northern Lights, Snow Pond public beach and boat landing.
Popular amenities for Winslow holiday rentals
Stay near Winslow's top sights
Other great holiday rentals in Winslow

Main Street Penthouse

2 Bedroom Apartment

Minutes to Colby/ Main Street

Cozy Maine Cabin With Lake Views (No Water Access)

Cozy apartment -Waterville Maine

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 | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €51 | €98 | €100 | €61 | €70 | €94 | €68 | €61 | €48 | €42 | €26 | €72 |
| 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 apartment rentals in Winslow?
Experience the best of Winslow with our apartment rentals, starting at about $40 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 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.
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
- Belgrade Lakes Golf Club
- Black Mountain of Maine
- Lost Valley Ski Area
- Sugarloaf Golf Club
- Range Ponds State Park





