
House vacation rentals in Winslow
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Quick stats about house rentals in Winslow

Total vacation rentals
Explore 40 vacation rentals in Winslow

Nightly prices starting at
Winslow vacation rentals start at G$2,088 GYD per night before taxes and fees

Verified guest reviews
Over 840 verified reviews to help you choose

Wi-Fi availability
40 of Winslow vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winslow rentals
Top-rated house rentals in Winslow
Guests agree: these houses are highly rated for location, cleanliness, and more.

Lakefront: Private Hot Tub, Sauna & Free Massages!
Make memories at our updated, 2500 sq. ft., lakefront home. Use our kayaks, canoes & peddle boats for the family! Great fishing - 648 acre lake. We offer many outside games, range of indoor games & arcade systems. Amazing 4-seasons room with outdoor dining setup viewing the lake. Enjoy our new hot tub, and grilling deck right outside master bedroom. Lavish soaking tub in master bath. Only 4 minutes to golf, 10 minutes to capital city, Augusta, and 45 minutes to skiing as well as Atlantic Ocean!

Cute Midcoast Cottage w Hot Tub
Kick back and relax in this ideally located modern cottage. Enjoy a soak in the hot tub or the peace of the covered porch. Situated in the heart of midcoast Maine, this cottage has it all. An elegant kitchen that awaits your culinary delights, a spacious living area, a primary bedroom with a TV, a kingsize bed and a luxurious bath with a soaking tub and a walk-in rainfall shower, plus twin bunk beds for the kiddos. A small store and a farm to table restaurant are conveniently across the street.

Modern Lakefront Home w/ Hot Tub • Summer Vacation
Grace's Cottage is a charming 1860's cottage on Lake Saint George. Newly remodeled, the 3 bedroom, 1 bath cottage offers a perfect blend of old-world charm and modern amenities. A spacious screened porch overlooks the lake, and a year-round hot tub provides a perfect spot to relax & unwind. This living space is perfect for gathering with family & friends. Whether you're seeking a romantic getaway or a fun-filled family vacation, Grace's Cottage is the perfect home base for your Maine adventure.

Farm house, River, Island, animals & private Chef.
MARCH-APRIL DAILY. Medicine Hill is a 136 acre farm on the Sandy River complete with a swimming hole and an entire island to explore. We grow vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch unwinding and taking it all in. 4 private bedrooms have stunning views surrounded by trees or fields. And if the Chef is available..EAT!!!

Lakefront 3 bedroom pet friendly on Messalonski
Make memories of a lifetime at this unique and cozy family-pet-friendly private lakefront on Messalonskee. Beautifully manicured lawn/gardens with a fire pit surrounded by the peaceful sounds of nature. A large dock to take in the spectacular views of bald eagles, loons, and blue herons. Owners boat is attached for occasional boat rides. This guesthouse is newly built with a covered porch overlooking the serene lake. Comes w/3 kayaks, 2 paddle boards, a paddle boat, life jackets, and a canoe

Carriage House
Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.

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 .

Waterfront Lakehouse with Hot Tub and Barrel Sauna
This unique lake house sits directly on the shores of Messalonskee Lake, just a half mile walk (or paddle!) to Snow Pond Center for the Arts and just a 10 minute drive from Colby College and Waterville. The house features multiple lake view decks, a hot tub overlooking an outdoor waterfall and gardens, a wood fired pizza oven, and an outdoor barrel sauna. There is a beach area for easy access into the water as well as a large dock and paddle board and kayaks. Incredible sunsets!

The Barn
I call my place "The Barn" because as I was finishing it it took the shape and feel of a barn. It's not a barn. It's a quiet post and beam open concept building (a Jamaica Cottages kit) set among the fields of Appleton, Maine. You'll sleep in the loft or on a futon on the main floor. The bathroom is huge, 10X10, with a heated floor. It's an open concept kitchen and living space. From Appleton you are 20 miles away from the tourist destinations of Camden, Rockland, and Belfast.

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.

Secluded Retreat w/ Luxe Hot Tub & Forest Views
Tucked near the woods of Maine, this peaceful cabin offers the perfect escape. Soak in the private hot tub under the stars, curl up by the electric woodstove, or work remotely with fast Wi-Fi and forest views. The cabin features a comfy king bed, full kitchen, clean modern bath, and self check-in. Enjoy your morning coffee in the sunroom or take a short drive to explore Belfast and the coast. Quiet, cozy, and surrounded by nature—ideal for rest, romance, or reflection.

The Barnhouse with hot tub
Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.
Popular amenities for Winslow house rentals
House rentals with a pool

Large private area, close to Rockland

Riverway Cottage

House in the woods

Home away from home

Pool, Dream Home Gym, TV+Desk Each Room, Games

Gorgeous house with a view

Stay Together in Style

Maine Lakehouse Retreat with pool
Weekly house rentals

Classy AF Home, walk across the street to Colby!

Halcyon Ridge

Family's Paradise: 3BR/2BA,Game Room & Lake Access

Red Cedar Haven | Lakefront • Dock • Kayaks

Cozy Waterfront Cottage

Lakefront Cottage on China Lake

Single Family on ThreeMile Pond

The Lake House on McGrath Pond | 4BR | Waterfront
Private house rentals

Country Charm, City Convenience

The HideAway - Starks

Antique Barn Apartment at Salt Water Farm

Misty Shores at North Pond

Red Barn at The Appleton Retreat

River House with King Beds & Fire Pit!

Cozy Lakefront Cabin on a Pond in Augusta, Maine

Lounging Loon
When is the best time to visit Winslow?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$4,802 GYD | G$5,220 GYD | G$5,637 GYD | G$5,637 GYD | G$6,264 GYD | G$9,396 GYD | G$5,220 GYD | G$7,308 GYD | G$11,484 GYD | G$6,264 GYD | G$4,802 GYD | G$4,593 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 |
Destinations to explore
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- 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





