Vacation rentals in Winthrop

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

A private clean tranquil cottage, dock, parking, deck, grill, hammock, kitchen & all amenities, bathroom, 2 bedrooms, sleeps 5, futon, WIFI, cable, bidet, washer & dryer, granite outdoor table, kayaks, paddle boards, floats, fire pit and fireplace. Minutes from great restaurants, bars, hiking trails, and shopping. The most amazing sunsets. 30 minutes from Portland. Winter rentals as well. 40 min. from Shawnee Peek, 1 mile from Seacoast tubing. This place is privately yours. Smoke free please!

5 out of 5 average rating, 87 reviews

A private deck features several black Adirondack chairs arranged for comfort, facing a panoramic view of a sunset over rolling hills and a lake. Soft lighting from string lights enhances the inviting atmosphere of the space.

Home in Woodstock

#1 View in Maine, Theater, HTub, Xbox, Golf, Lake

Welcome to the Sunday River retreat in our luxury chalet with the best views in Maine. Our sanctuary can comfortably sleep 12 and boasts Lake Christopher panoramic views with Mt. Abram sights. Minutes from Sunday River Resort, a public boat launch and other area attractions. Private hot tub, fire pit, wood stove and deck await your arrival. Enjoy arcade games, Xbox, a movie theatre room, BBQ grill and speakeasy theme bar setup. Don't forget to take a picture in the gondola and to catch a sunset!

4.83 out of 5 average rating, 35 reviews

The exterior of a modern home is showcased, surrounded by greenery and set against a clear blue sky. Below, a serene beach area leads to calm waters, with rocks scattered along the shoreline. An open-concept living space is visible, featuring a well-equipped kitchen and a cozy seating area.

Cabin in Standish

Updated home near sandy beach on Sebago Lake

Escape to this charming, pet-friendly Sebago Lake retreat, offering a peaceful getaway for up to 8 guests. This modernly updated 3 bedroom. 1 bathroom is enough space for the whole family. Located just a short walk to the shores of Sebago, enjoy the included kayaks, SUP, beach access, and private dock. At the end of the day, relax in the spacious backyard listening to the tranquil brook running through, or gather around the fire pit creating lasting memories. Only 45 minutes to Portland, Maine!

4.94 out of 5 average rating, 126 reviews

Home in Windham

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

4.92 out of 5 average rating, 74 reviews

A modern kitchen is displayed, featuring a central wooden island with two stools. Stainless steel appliances, including a refrigerator and oven, are complemented by white cabinetry and a tiled backsplash. Natural light floods the space, accentuating the clean lines and functionality of the area.

Apartment in East End

East End Rental, Portland, Maine

Visit Portland, Maine! We offer a nicely renovated, quirky, third floor (two flight walk-up) three bedroom living space as a vacation rental. East End - Congress Street, foot of Munjoy Hill, city side (near Otto's East End Cafe). Great area! Very sunny non-smoking building with panoramic views of the city and water! Private, brick side walk and courtyard with zen gardens to relax in. Steps away from bakeries, coffee shops, restaurants, yoga studios and shopping. STR Registration #2018-3625

4.94 out of 5 average rating, 62 reviews

A charming exterior of a two-story house is framed by a well-maintained garden filled with vibrant flowers and greenery. The house features a mix of gray and red siding, with multiple windows allowing ample natural light. A gravel pathway leads to the entrance.

Guest suite in Hanover

Mystery Mountain View Near many outdoor activities

Put up your feet at this 900 sqft rental unit with 1 large bedroom, full kitchen, media room, sitting room, full bath, dining area, and dart board. Private entrance, daylight basement in lower level of our home. There is a key code box to obtain access, and guest parking. 15 minutes to Sunday River and Black Mountain and 20 minutes to Mt. Abram ski resorts. Swimming access at Howard Pond. Skiers, riders, hikers, kayakers, and outdoor enthusiasts would love this location anytime of the year.

4.92 out of 5 average rating, 13 reviews

A wooden dock extends into a calm lake, surrounded by lush green mountains. A boat is tied next to the dock, while a lounge chair sits invitingly on the platform. The water reflects the serene landscape, creating a peaceful atmosphere.

Cabin in Greenwood

All seasons Lake House next to ski areas

Welcome to the Howell’s cabin ! A beautiful and peaceful lake house in the heart of Maine. Located just 5 minutes from Mt Abrahm ‘s ski area , 20 minutes from Sunday River Ski Center, and 15 minutes from Bethel, a charmy town with great restaurants and unique attractions. This has been our family getaway for nearly 40 years. Recently renovated, fully equipped kitchen, tiled bathroom, heating/ AC system, Wi-Fi and a nice deck to enjoy your morning coffee. No suitable for infants under 6

4.83 out of 5 average rating, 6 reviews

Home in Boothbay

Tailwinds - Upscale Oceanfront! Stunning Views!

Welcome to Tailwinds in East Boothbay, where you will enjoy stunning sunsets over Linekin Bay from the comfort of this beautifully updated home. Formerly a B&B, this is a perfect place to gather frinds and family with en-suite baths 2 living rooms and a large porch. You will also find all new beds and furniture, luxurious 100% cotton linens, and AC window units in the bedrooms. Located between downtown Boothbay Harbor and Ocean Point, this is a gorgeous spot for your next family vacation!

5 out of 5 average rating, 6 reviews

A wooden dock extends into a calm lake, leading to a small boat anchored at the end. The water reflects a clear blue sky, with gentle ripples across the surface, and green hills visible in the distance.

Home in Harrison

2BR Lake House on Private Beach w/hot tub & sauna

Romantic getaway or peaceful family vacation, this lake house is right on a private beach, and perfect all year round!The beach is literally your back yard! Experience beautiful views while enjoying a cozy outdoor fire. Relax and take amazing sunset pics in the covered hot tub, or unwind indoor w/the sauna and fire place. Cook up a delicious meal in the fully stacked kitchen. Centrally located near hiking trails, and 45min from North Conway outlets. Book now and make memories! ✨

4.82 out of 5 average rating, 11 reviews

Chalet in Woodstock

Cozy Mountainside Retreat– come explore & Relax!

Welcome to Your Summit Retreat Suite! • Large, cozy fireplace • Spacious loft • Well-appointed, eat-in kitchen • Fiber-optic WiFi & Smart TV • Large enclosed back porch • Baby gear & kid-friendly games • Pets considered for additional fee Nestled in the heart of the western Maine mountains, our home is minutes away from top-tier ski resorts: • Mt. Abram (5 minutes) • Sunday River (15–20 minutes) • Black Mountain (30 minutes) We look forward to hosting your group!

5 out of 5 average rating, 62 reviews

A historic house with a charming exterior is set amidst lush green lawns and colorful trees. A stone pathway leads to the entrance, flanked by well-maintained shrubs. A spacious front porch is adorned with a stylish railing and seasonal decorations.

Home in Bethel

Dream Vacation Home - Full Amenities & Hot Tub

The Bingham House in Bethel / Sunday River is the ultimate vacation home to meet all your needs. Sleeps up to 18 people in 6 bedrooms, 6 bathrooms. Full service amenities include: wifi, 10 HD TVs with premium cable (including HBO), 8-person hot tub, fire pit, billiards room, bar w/ wine fridge, game room, elevator, full kitchen & walk-in pantry, gas grill, fireplaces, parking, free shuttle to Sunday River, crib + high chair + booster seat

4.83 out of 5 average rating, 139 reviews

A bright dining area features a large glass table surrounded by six black wooden chairs. Natural light filters through three large windows, and a simple floral centerpiece sits at the table's center. A modern chandelier hangs above, complementing the neutral-toned walls.

Apartment in East End

Fall in LOVE With PORTLAND, MAINE

Portland and its surrounding areas is a FOODIE's paradise. Our comfortable home is perfect for Family or Friends to enjoy Portland's charm. Approx 3 miles from Portland Jetport and 90 miles from Boston Logan airport. Walk to downtown or the Old Port on the waterfront. The surrounding areas offer fine beaches and beautiful scenic towns guaranteed to make you want to come back and visit this best kept secret again!

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Popular amenities for Winthrop vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Winthrop's top sights

Hannaford Supermarket37 locals recommend

Fielder's Choice Ice Cream9 locals recommend

van der Brew9 locals recommend

FAST EDDIES DRIVE IN8 locals recommend

Lakeside Orchards7 locals recommend

Winthrop House of Pizza6 locals recommend

Other great vacation rentals in Winthrop

5 out of 5 average rating, 15 reviews

A covered entryway is situated beneath an upper porch, featuring a wooden bench beside a welcoming door. A stack of firewood is neatly arranged to the right, partially covered with a tarp. Soft lighting illuminates the space, accompanied by scattered autumn leaves.

Home in Greenwood

Cozy Greenwood Condo!

5 out of 5 average rating, 103 reviews

An outdoor seating area is presented with a spacious sectional sofa made of dark wicker, positioned under a covered patio. The lawn extends towards the private sandy beach and dock by the lake, with a view of kayaks and trees in the background.

Cottage in Belgrade

Lakefront Home, Sandy Beach, Belgrade Lakes Maine

4.97 out of 5 average rating, 63 reviews

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

4.75 out of 5 average rating, 20 reviews

A covered porch features a comfortable seating area with a wicker sofa and matching cushions, arranged around a low coffee table. A hammock is suspended for relaxation, and a striped outdoor rug adds texture to the wooden floor. Large windows provide views of the surrounding landscape.

Home in Otisfield

Log Cabin *15 acres*hunting* snowmobile*skiing

5 out of 5 average rating, 3 reviews

The sun sets over Great Moose Lake, casting warm orange and golden hues across the water's surface. Reflections of the sunlight dance on the rippling waves, while silhouettes of trees mark the shore in the distance.

Home in Hartland

The Great Moose in Stunning Maine Swim, Fish & Ka

5 out of 5 average rating, 101 reviews

Two black Adirondack chairs are positioned around a stone fire pit on a stone patio. In the background, a serene view of Winnegance Creek is visible, framed by trees and a cloudy sky.

Home in Bath

Waterfront Farmhouse with Modern Flair!

4.93 out of 5 average rating, 43 reviews

The interior features natural wood paneling with exposed beams overhead. A plush sectional is positioned in front of a flat-screen television, surrounded by sunlight from multiple windows. A round dining table complements the space, creating a welcoming area for relaxation and family gatherings.

Cabin in Madison

Lovely,private cabin w fire pit, bbq on 30 acres