House vacation rentals in Winslow

4.97 out of 5 average rating, 177 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.

4.96 out of 5 average rating, 163 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!

5 out of 5 average rating, 106 reviews

An aerial view captures the coastal cottage set on a granite ledge beside the Penobscot River. Surrounding trees in autumn hues frame the property, and the tranquil water reflects the colorful foliage, creating a serene natural setting.

Home in Hampden

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private sanctuary where tranquility meets luxury. Our Coastal Maine Cottage home is perched on a granite ledge that disappears twice daily with the rising tide. Enjoy the pristine interior bathed in natural light, cherry floors, and gourmet kitchen. Wake to panoramic views of the Penobscot River from the owner's suite. Conveniently located 12 minutes to downtown Bangor, our retreat offers easy access to urban amenities, an international airport, and Acadia! IG @cozycottageinmaine.

4.96 out of 5 average rating, 137 reviews

An open living area features a vaulted pine ceiling and large windows providing natural light. A dining table and chairs are placed next to the kitchen, with a cozy seating area that includes a comfortable couch. A modern entertainment unit with a TV is present.

Home in Sumner

Family Getaway in Oxford Hills-Dog Friendly!

Experience this 2BR/2BA retreat, perfect for couples and small families. Nestled among nature, this hillside getaway offers privacy, modern comforts, and a peaceful ambiance. Unwind by the fireplace, fire pit, relax on the deck, or explore the great outdoors with your furry friend (guests may bring 1 dog). Whether you're seeking outdoor adventure or relaxation, this hideaway is the perfect home base for your next getaway. Families of 5 or 6 can be accommodated with the queen size pull out sofa.

4.92 out of 5 average rating, 131 reviews

A spacious farmhouse exterior is illuminated by warm lights against the evening sky. The porch features several wooden chairs, inviting relaxation. Large windows reveal the welcoming interior, surrounded by lush greenery.

Home in Starks

Heavenly spacious 4bd farmhouse with river!

Medicine Hill is a 125 acre farm on the Sandy river complete with an old fashioned swimming hole and an entire island to explore. We grow a wide variety of 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 taking it all in. 4 bedrooms have incredible views and are surrounded by trees or fields. And if the Chef is available..eat!

4.97 out of 5 average rating, 236 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.

4.95 out of 5 average rating, 133 reviews

A two-story house showcases a charming design with a gray exterior and red front doors. Green trees frame the property, providing a natural backdrop. The inviting driveway leads to the entrance, with windows allowing for ample natural light.

Home in Oakland

The Modern Maine Retreat

Stay at our Maine Getaway. Our fully renovated 1940s New Englander is sure to bring you peaceful vibes and luxury. Come play Pickleball with just a quick walk over to the courts, driving not necessary!Close to downtown Waterville, Colby College, Thomas College, UMaine Farmington. 2 min from Messalonskee Lake boat launch where you can boat, kayak, canoe, & ice fish. Proximity to ski mountains, Titcomb, Black Mountain, Sugar Loaf & Sunday River. Please note BBQ is only accessible May-October.

4.98 out of 5 average rating, 143 reviews

A spacious bedroom features a large bed with blue bedding against a dark blue accent wall. Two bedside lamps provide soft lighting. A comfortable leather armchair is positioned next to a small nightstand, which holds a tissue box and a framed print.

Home in Hallowell

Hilltop Retreat with A/C, Hot Tub & Sauna

Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub or infrared sauna, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

4.99 out of 5 average rating, 215 reviews

A cozy living area features knotty-pine walls and a comfortable seating arrangement with a blue sofa. A small coffee table sits atop a textured area rug. A television is positioned on a media console, illuminated by a nearby lamp. Two windows with patterned curtains allow natural light to fill the space.

Home in Farmington

Farmington! Walk to town & trails! Family-Friendly

We take great pride in providing a stay that you will remember for years to come. Our moose house is well-stocked with all essential amenities and a few extra surprises! Quaint, convenient neighborhood walking distance to UMF and downtown Farmington. Franklin Memorial Hospital is a short drive. Sugarloaf and Rangeley areas are 45 minutes. WIFI and smart TVs. (No cable.) Washer/Dryer with detergent available. Great place to stay for exploring Maine or a visit with your family and friends.

4.96 out of 5 average rating, 184 reviews

A red, two-story building is set among vibrant autumn trees, with hues of orange, yellow, and green. The structure features multiple windows and a covered porch, surrounded by a grassy field showcasing its peaceful rural setting.

Home in Appleton

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.

4.85 out of 5 average rating, 203 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. 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 .

4.86 out of 5 average rating, 100 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.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Winslow house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 316 reviews

A clear blue swimming pool sits within a wooden deck, surrounded by lush greenery and a white privacy fence. A shaded seating area features comfortable lounge chairs, inviting relaxation in the sunlit outdoor space.

Home in Bangor

Cozy, fun, 3 bedroom home with a pool and Hot Tub.

5 out of 5 average rating, 10 reviews

A modern kitchen showcases white cabinetry paired with a stylish granite countertop. Dark appliances and a unique tile backsplash complement the rustic wooden beams overhead. An island with a sink offers additional workspace, while an inviting rug adds warmth to the overall design.

Home in Windham

New Listing! Pool, Hot tub & Lakes! Mins to Sebago

4.91 out of 5 average rating, 81 reviews

A spacious blue house is set against a backdrop of lush green grass and trees. The property features a landscaped front area with various shrubs and stone walls, inviting outdoor seating arrangements, and a clear sky above, enhancing the serene atmosphere.

Home in Liberty

Luxe Liberty: Getaway with Heated Indoor Pool!

4.87 out of 5 average rating, 15 reviews

A swimming pool is surrounded by paved decking, with several lounge chairs positioned throughout. A green umbrella offers shade near the poolside, and lush landscaping with trees and flowering plants is visible in the background, complemented by a clear blue sky.

Home in Lincolnville

Coastal Retreat with Pool and Cheerful Vibes

5 out of 5 average rating, 24 reviews

The backyard features an above-ground pool surrounded by a spacious deck, offering ample seating and relaxation areas. A shaded dining space is visible under an umbrella, while the two-story colonial home stands in the background, framed by lush greenery.

Home in Mechanic Falls

Lovely home with hot tub and pool

5 out of 5 average rating, 12 reviews

The exterior of the property features a classic white façade with multiple gabled roofs and a porch adorned with rocking chairs. Lush greenery surrounds the house, complemented by flowering plants along the pathway leading to the entrance.

Home in Newcastle

The Flying Cloud

4.92 out of 5 average rating, 12 reviews

A stone pathway winds through a lush garden adorned with colorful flowers and greenery. Natural rocks are integrated into the landscape, while wooden barrels add a rustic touch. In the background, a pool is partially visible, set against a backdrop of trees.

Home in Washington

House in the woods

4.95 out of 5 average rating, 60 reviews

An outdoor space is highlighted by a heated saltwater pool surrounded by a wooden deck. Comfortable seating options are arranged nearby, complemented by a large umbrella for shade. Lush greenery and a mature tree provide a natural backdrop, enhancing the inviting atmosphere.

Home in Rockport

Ocean View Retreat with Pool / Hot Tub

Show all

Weekly house rentals

4.96 out of 5 average rating, 25 reviews

The exterior of Manor House is highlighted, showcasing a charming 1900's design with a large front porch and steps leading to the entrance. An American flag is displayed prominently, while decorative bunting accents the porch. Surrounding greenery adds to the inviting atmosphere.

Home in Rome

Manor House on Long Pond with water toys!

5 out of 5 average rating, 6 reviews

An inviting living room features a modern blue sectional sofa and a cozy round chair. A unique branch with lights hangs overhead, creating a soft glow. Large sliding doors open to the backyard, with seating visible beyond, allowing natural light to brighten the space.

Home in Belfast

The River House – private, fire pit, 5 min to town

5 out of 5 average rating, 7 reviews

A spacious wooden deck is surrounded by lush green trees, featuring a large dining table with six chairs and a grill. A fire pit is located at the center, surrounded by four vibrant green chairs. A cozy atmosphere is conveyed with a patterned outdoor rug.

Home in Rome

Belgrade Lake house with Dock!

4.86 out of 5 average rating, 59 reviews

A cozy living area features a blue sofa facing two red chairs across a small round table. A bookshelf filled with various books is positioned against a wall. Natural light enters through multiple windows, casting a warm ambiance on a geometric patterned rug.

Home in Skowhegan

Court and Cross

4.86 out of 5 average rating, 70 reviews

A spacious living area features a wooden ceiling and a stone accent wall. A dining table with metal chairs is positioned near large windows, allowing natural light to fill the space. A cozy seating area includes a gray couch and a mounted TV, contributing to a welcoming atmosphere.

Home in Burnham

The Maine Lake House with an Amazing Sand Beach!

4.89 out of 5 average rating, 83 reviews

A spacious screened porch is featured, furnished with comfortable seating and a swing bed dressed in soft linens. Large windows allow natural light to fill the area, complemented by a view of the surrounding nature through the screening.

Home in Liberty

Modern Lake Front Home with Hot Tub

5 out of 5 average rating, 55 reviews

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.

Home in Oakland

Lakefront 3 bedroom pet friendly on Messalonski

5 out of 5 average rating, 23 reviews

The exterior of the house is presented, featuring a green metal roof and a large driveway leading to a two-car garage. Lush green grass surrounds the home, while trees and a clear blue sky enhance the peaceful rural atmosphere.

Home in Cornville

Modern Cornville Ranch

Show all

Private house rentals

4.81 out of 5 average rating, 16 reviews

A charming two-story house features a light pink exterior and white trim, surrounded by manicured grass. The welcoming front steps lead to a spacious porch, and the property is complemented by several trees, providing a pleasant outdoor environment.

Home in Newport

Pretty Old House

4.94 out of 5 average rating, 33 reviews

A country home is positioned against a backdrop of lush greenery. A sign marked '45' is visible, while a sloping yard leads to the house. The structure features dark trim and large windows, with ample natural light filtering through the surrounding trees.

Home in Stetson

1 Bedroom Country Stay Fresh & Modern for 4 Guests

5 out of 5 average rating, 17 reviews

An outdoor area features a gravel patio surrounded by trees. Red Adirondack chairs are arranged around a fire pit, with a picnic table nearby. The exterior of the cottage showcases wooden shingles, large windows, and a welcoming entrance.

Home in Rome

Newly built in 2024, Long Pond lake access

5 out of 5 average rating, 15 reviews

Two kayakers enjoy a peaceful paddle on Sibley Pond, surrounded by lush greenery. Each kayak is brightly colored in orange and yellow. The calm water reflects the overcast sky, creating a serene backdrop for outdoor activities.

Home in Canaan

Zeus's Landing| Lakefront | Close to Colby

4.67 out of 5 average rating, 3 reviews

A contemporary structure features a striking red exterior, with multiple large windows allowing for abundant natural light. A wooden deck extends from the upper level, offering outdoor seating. The surrounding landscape includes rocky terrain and trees, complementing the sleek design.

Home in Appleton

Red Barn at The Appleton Retreat

4.89 out of 5 average rating, 70 reviews

A modern two-story house is set among trees, featuring a balcony overlooking a lake. A wooden dock extends into the water, with a small boat and red kayak resting on it. The tranquil scene is framed by the greenery of the surrounding area.

Home in Washington

New all season lakefront house on Washington Pond

5 out of 5 average rating, 4 reviews

Two white Adirondack chairs are positioned on a wooden deck, facing a scenic view of the water. The grassy area in front leads to the waterfront, framed by green trees on either side and a cloudy sky above.

Home in Friendship

Renovated Cottage w/waterviews - Fall Sale!