Holiday houses in Winslow

A dining area is presented with a large wooden table, surrounded by metal chairs. Natural light enters through a nearby window, illuminating the space. A decorative bowl filled with flowers sits at the center of the table, enhancing the inviting atmosphere. Simple wall art complements the decor.

4.99 out of 5 average rating, 137 reviews

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.

LocationValuePets

4.83 out of 5 average rating, 6 reviews

Home in China

100 Ft Private Sandy Beach | Newly Renovated 4BR R

This charming two-story lakefront home blends classic character with a peaceful, natural setting, offering a true retreat-like feel. Ideally located in the heart of China Village, it combines small-town charm with the tranquility of lakeside living. Its timeless design reflects a complementary architectural style, simple, balanced, and well-suited to its surroundings, creating a warm and inviting presence. Set on a generous lot, the property features a wide, open lawn perfect for outdoor games,

FamilySleep qualityKitchen

5.0 out of 5 average rating, 111 reviews

Condo in Oakland

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.

LocationFamilyTV

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 .

FamilyValueLong stay

5.0 out of 5 average rating, 38 reviews

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.

Home in Belgrade

Enjoy a gorgeous sunset steps away from Great Pond

Relax, swim, boat, kayak and enjoy time with your family at beautiful Great Pond Lake. This home is located steps from Great Pond and has 3 lovely decks from which to enjoy the sunset. Great Pond is located only an hour North of Portland in Belgrade Maine. Belgrade Lakes Golf Club is one of the top rated courses in Maine and is a public course. There is easy access to multiple hiking trails. There are also many winter activities - snow shoeing, cross country skiing and ice skating!

ValueFamilySleep quality

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

Unwind year-round at this stunning lakeside home on McGrath Pond with 100+ ft of private water frontage. Sleeps 10 with 4 spacious bedrooms. Enjoy an open floor plan, fully equipped kitchen, large deck with lake views, WiFi & cable TV. Near Colby College and a short drive to Sugarloaf, Acadia, Bar Harbor & Freeport (LL Bean and outlets). Whether you're kayaking in summer, leaf-peeping in fall, or skiing in winter, this home has everything you need for a memorable Maine escape.

LocationFamilyAccuracy

Superhost

Apartment in Winslow

Entire 3 BR apartment in Winslow| 2nd FL | 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

LocationValueHospitality

4.78 out of 5 average rating, 9 reviews

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.

LocationFamilyQuiet

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

Enjoy easy access to everything from this centrally located 3 bedroom/2.5 bath home. Newly renovated, very spacious sunlit home only 2 miles from I-95, public beach 1 mile, Colby College 6 miles, Thomas College 3 miles, Waterville 3 miles, Augusta 15 miles, and in the heart of the Belgrade Lakes chain. Many food options in all directions. Clean, comfortable, open, bright, and includes a private yard. This home sleeps up to 6 guests with its 3 queen beds.

FamilyLocationDecor

4.9 out of 5 average rating, 174 reviews

A corner of the enclosed front porch showcases a wicker chair adorned with a colorful throw blanket. A small, coral-colored table holds a coffee cup, while a potted plant adds a touch of greenery. Natural light streams through the large windows.

Home in Waterville

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.

ValueFamilyWalkability

4.92 out of 5 average rating, 65 reviews

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.

LocationFamilySleep quality

4.95 out of 5 average rating, 85 reviews

Classy AF Home, walk across the street to Colby!

THE BOOKING CALENDAR OPENS ONE YEAR IN ADVANCE, INCLUDING GRAD WEEKEND. Lovingly renovated three bedroom home across the street from Colby College’s Senior Drive. My grandfather built our house in the 40’s, we have done all of the renovations ourselves to create open, inviting spaces with unique touches while maintaining the original footprint. Our home is a labor of love that we hope YOU love. *Pets ok w/ notice and 50$ fee*

LocationFamilyAir conditioning

Popular amenities for Winslow holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Winslow

The entrance to the apartment features a red door framed by two white columns. A small planter with pink flowers sits beside the door. The porch has a wooden floor and is partially covered, offering shelter from the elements.

5.0 out of 5 average rating, 41 reviews

Clean & Comfortable, 2nd Fl Apt

FamilyLocationCheck-in

4.8 out of 5 average rating, 10 reviews

Home in Vassalboro

Dragonfly Haven at ThreeMile Pond

LocationFamilyOutdoor spaces

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.

4.92 out of 5 average rating, 156 reviews

Updated 4br Family Home Near Belgrade Lakes

FamilyValueAir conditioning

4.83 out of 5 average rating, 12 reviews

Cozy Uptown Waterville

LocationValueComfort

Home in Winslow

Waterville Oasis Near Colby College & Hospitals

LocationNearbyHospitality

5.0 out of 5 average rating, 3 reviews

4.97 out of 5 average rating, 39 reviews

A well-appointed kitchen displays a central island with a light-colored countertop and green cabinetry. Wooden beams in the ceiling add character. A door with windows leads to an outdoor area, while neutral tones in the walls create a clean and open atmosphere.

Home in China

The farmhouse

FamilyLocationAmenities

5.0 out of 5 average rating, 10 reviews

Home in Waterville

Norman House

LocationFamilyCleanliness