House vacation rentals in Winslow

4.96 out of 5 average rating, 231 reviews

A large blue house with multiple sections is pictured beside a clear lake. A private dock extends into the water, and outdoor seating in the form of two chairs is visible on the lawn, surrounded by lush trees.

Home in Augusta

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!

4.94 out of 5 average rating, 241 reviews

A log cabin is situated on a grassy expanse beside the water, surrounded by trees displaying vibrant autumn foliage. A private dock extends into the lake, providing access for boating activities, while the spacious lawn offers plenty of room for outdoor enjoyment.

Home in Stetson

Lakefront Log Cabin on Pleasant Lake

Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

4.98 out of 5 average rating, 274 reviews

A charming modern cottage with a red exterior and a pitched roof stands amidst lush greenery. The covered porch is furnished with comfortable seating, inviting relaxation. Large windows allow natural light to enter, enhancing the welcoming atmosphere of the property.

Home in Northport

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.

4.94 out of 5 average rating, 171 reviews

A spacious farmhouse stands amidst a grassy area, illuminated by warm light from numerous windows. A covered porch extends along the front, featuring wooden chairs. The surrounding landscape includes mature trees providing a natural backdrop.

Home in Starks

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!!!

4.87 out of 5 average rating, 120 reviews

A hot tub bubbling gently is positioned on lush green grass, with a serene view of Lake Saint George in the background. Colorful autumn trees line the water's edge, and a clear blue sky adds to the tranquil setting.

Home in Liberty

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.

4.94 out of 5 average rating, 178 reviews

An aerial view of a lakefront cottage surrounded by lush greenery and a clear lake. A dock can be seen with two boats, and the cottage features large windows that reflect the sunlight. The peaceful setting is complemented by the serene water and shoreline.

Home in Liberty

The Pearl of Lake Saint George

Enjoy this beautiful lakefront cottage on pristine Lake St. George with amazing sunrises. The home is year round and heated. Less than a mile from Lake St. George Brewing Company, John’s Ice Cream, and Lori’s Café, the state park and boat launch is also less than three miles away. First floor has 1 bedroom (queen bed), a full bathroom, full kitchen with all essentials, and utility room with a washer and a dryer. The second floor has a half bath and three bedrooms (king, and two queen beds).

4.97 out of 5 average rating, 328 reviews

The open-concept living area showcases natural wood walls and a ceiling, with large windows allowing ample light. A soft sofa and a daybed are arranged around a round coffee table on a striped area rug. A staircase leads to the upper level, visible in the background.

Home in Farmington

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.

4.98 out of 5 average rating, 209 reviews

A serene waterfront view captures calm waters reflecting the sky and surrounding landscape. Lush greenery is visible along the shore, while scattered clouds drift across the blue sky. The tranquil scene invites relaxation and appreciation of nature.

Home in Newcastle

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

Waterfront Retreat with Gorgeous Views Stunning 3-bedroom, 2-bath home perfect for multi-generational gatherings. Features an open-concept layout, chef’s kitchen, 1st-floor bedroom and bath, 2nd floor with 2 bedrooms and 1 bath. Kayak from your backyard, hike nearby trails, or swim in Damariscotta Lake just a 5-minute walk away. Stay connected with high-speed fiber optic WiFi. Close to charming Newcastle and Damariscotta shops and restaurants. A true oasis for nature and relaxation lovers!

4.87 out of 5 average rating, 239 reviews

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

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 .

4.96 out of 5 average rating, 130 reviews

A wooden dock extends into calm water, reflecting the clear blue sky and surrounding greenery. Trees line the shore, creating a serene backdrop for peaceful moments by the water.

Home in Friendship

Maine Waterfront Hideaway

You won't find mobs of tourists here but you will experience a working lobstering village in Maine. Sit back, relax and enjoy the quiet and privacy of 2+ acres at the end of a dirt road with a huge dock located on a tidal cove. Great for family reunions with lots of space and activities for folks of all ages. We focus on making the house comfortable and don't want you to worry about the little things like feet on the couch, water rings on the table or a broken glass. Life happens :-)

4.85 out of 5 average rating, 112 reviews

A serene view of a lake at sunset is presented, showcasing soft hues of orange, pink, and purple reflected on the water. Silhouettes of trees line the shore, while the calm surface creates gentle ripples, inviting relaxation and contemplation.

Home in Manchester

Lakeside retreat on quiet cove on Cobbessee Lake!

Nothing beats summer days on the lake in Maine. Not only is this lake home situated on a quiet cove on central Maine's Cobbossee Lake, but it is near amenities in Augusta and close to I-95! Enjoy two large docks, a large lawn and gently sloping swimming area, and a newly renovated five bedroom house with two full bathrooms. This is the Maine vacation home you are looking for! Two of the bedrooms and one bathroom are in the basement, which is still under some small construction.

4.86 out of 5 average rating, 117 reviews

A serene outdoor area is framed by lush greenery and trees, showcasing vibrant orange flowers in the foreground. A meandering stone path leads towards a gathering area in the distance, partially visible through the foliage.

Home in Sidney

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.

Popular amenities for Winslow house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 113 reviews

Home in South Thomaston

Large private area, close to Rockland

4.95 out of 5 average rating, 21 reviews

A single-story home is set against a backdrop of tall trees, featuring a front porch with white railings. The well-maintained lawn is complemented by a curved garden bed with mulch and shrubs, creating a welcoming exterior.

Home in Skowhegan

Home away from home

5.0 out of 5 average rating, 24 reviews

Home in New Portland

Riverway Cottage

5.0 out of 5 average rating, 44 reviews

The house is set on a grassy hill, surrounded by neatly trimmed bushes and rocks. A welcoming porched area wraps around the front, and the roof features dormer windows. The backdrop consists of a clear blue sky with scattered clouds, creating an inviting atmosphere.

Home in Belfast

Gorgeous house with a view

5.0 out of 5 average rating, 10 reviews

Home in Lewiston

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

4.92 out of 5 average rating, 62 reviews

The exterior of a three-story colonial home is showcased, featuring a large circular pool surrounded by a white fence. Lush green lawn and trees provide a serene backdrop, while a spacious deck extends from the house, offering ample seating and relaxation space.

Home in Newport

Maine Lakehouse Retreat with pool

4.96 out of 5 average rating, 27 reviews

A gravel driveway leads to a white house nestled among tall trees. Lush greenery surrounds the area, creating a serene atmosphere. A pathway connects the house to the driveway, with steps visible leading up to the entrance.

Home in Washington

House in the woods

Superhost

The living area presents a blend of comfort and style, featuring a spacious gray sofa complemented by a wooden coffee table. A stone fireplace serves as a focal point, while built-in shelves display curated items. Natural light fills the space through large windows, enhancing the inviting ambiance.

Home in Lincolnville

Coastal Retreat with Pool and Cheerful Vibes

4.86 out of 5 average rating, 22 reviews

Weekly house rentals

A circle of white Adirondack chairs is arranged around a fire pit on a manicured lawn. Tall trees provide shade, and a serene lake is visible in the background, reflecting the soft light of the evening. The scene conveys a peaceful outdoor gathering space.

4.99 out of 5 average rating, 96 reviews

Lakefront 3 bedroom pet friendly on Messalonski

4.95 out of 5 average rating, 85 reviews

Classy AF Home, walk across the street to Colby!

An open living area features a cozy seating arrangement next to an elegant stone fireplace. A circular coffee table sits on a textured area rug, and large windows provide ample natural light. A kitchen island with bar stools is visible, allowing for casual dining.

4.98 out of 5 average rating, 45 reviews

Ultra Spacious and Hosts are Gracious

The lakeside cottage features multiple decks, offering expansive outdoor space and views of the surrounding trees. A terraced lawn leads down to the water's edge, where a rocky shoreline can be seen. The building's warm color complements the natural setting.

5.0 out of 5 average rating, 38 reviews

Enjoy a gorgeous sunset steps away from Great Pond

4.8 out of 5 average rating, 10 reviews

Home in Vassalboro

Dragonfly Haven at ThreeMile Pond

An outdoor deck is showcased, featuring a dining table surrounded by several chairs with colorful cushions. Potted flowers add vibrant touches, and a lounge chair is positioned nearby. Lush trees and a glimpse of the lake view are visible in the background, creating a serene atmosphere.

4.88 out of 5 average rating, 25 reviews

The Lake House on McGrath Pond | 4BR | Waterfront

A cozy living area features a light grey sofa with decorative blue pillows, complemented by two matching armchairs. Large sliding glass doors provide an inviting view of the outdoor seating area and the serene landscape by the lake. Natural wood paneling enhances the warm ambiance.

4.92 out of 5 average rating, 50 reviews

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

4.98 out of 5 average rating, 58 reviews

An outdoor dining area is featured with a sturdy table and chairs, shaded by a large umbrella. A grill is positioned nearby, with an expansive view of lush green hills and a clear blue sky stretching into the distance.

Home in Freedom

Halcyon Ridge

Private house rentals

The cottage features a spacious deck surrounded by tall trees, providing ample outdoor seating. Large glass windows reflect the natural surroundings and offer views of the lake. The structure showcases a mid-century modern design, harmonizing with the tranquil environment.

5.0 out of 5 average rating, 13 reviews

Lounging Loon

4.84 out of 5 average rating, 86 reviews

Home in Mount Vernon

Lakefront Retreat, Boat Rental & Dogs Welcome!

4.86 out of 5 average rating, 22 reviews

Salmon Lake Retreat

4.98 out of 5 average rating, 63 reviews

The exterior of the home is shown, featuring a two-story structure with large windows that welcome natural light. The surrounding landscaped yard includes lush greenery, flower beds, and a spacious deck. A wooded area provides a serene backdrop to the property.

Home in China

Loon Lodge On China Lake

Superhost

Home in Vassalboro

Cozy Waterfront Cottage

4.71 out of 5 average rating, 14 reviews

5.0 out of 5 average rating, 22 reviews

The exterior of a newly renovated duplex is showcased, featuring two large sections with ample windows. A spacious lawn framed by trees leads to a wooden deck with seating. Natural stone borders the yard, blending with the surrounding greenery.

Home in Northport

Double On The Rocks, ocean view family retreat

5.0 out of 5 average rating, 28 reviews

A charming cabin exterior is surrounded by lush trees, featuring natural wood siding and a gabled roof. The screened porch offers a welcoming entry with green trim and a white door, inviting guests to enjoy outdoor relaxation in a private setting.

Home in Rome

Wildewood Haven on beautiful Long Pond