
House vacation rentals in Winthrop
Find and book unique houses on Airbnb
Quick stats about house rentals in Winthrop

Total vacation rentals
Explore 30 vacation rentals in Winthrop

Nightly prices starting at
Winthrop vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

Verified guest reviews
Over 950 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Winthrop vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winthrop rentals

4.9 Average rating
Winthrop stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Winthrop
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!

Sunset & Lake View, Theater, HTub, Xbox, Mini Golf
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!

The GETAWAY, Rangeley
Our GETAWAY-perfect place for relaxing and fun! It’s private but 1/2 mile to IGA and approx 1 mi to beautiful downtown Rangeley with great restaurants, bowling, arcade, darts and shuffleboard. Ltd access to snowmobile trails directly from the house. ATV is no longer allowed from our home. Trails can be accessed from IGA (park across the st., or Depot Rd (includes trailer parking) 3/4 mile from our home. Hiking and incredible scenery! Walking distance to Pickford Pub and mins o Mtn Star Estate.

Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Beautiful lakehouse 2.5 h Boston, 40 min Portland
Beautiful lake living: 2.5 hours from Boston, 40 min. from Portland. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances, air conditioning. Minutes to Lewiston/Auburn - close to dining and stores. Spend your days swimming, canoeing, kayaking and fishing, use our grills or lobster pot to prepare your dinner and relax by the fire pit, toasting s'mores while watching the gorgeous sunsets.

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.

*1MMview*Bar,Hot Tub,3mins2Pleasant Mnt, Pool tab.
This special, completely renovated place can host your family gathering or group of friends in an inviting setting. This unique house with a private bar, spa, and a pool table will satisfy all your vacation needs! Located close to everything, but absolutely quite and private 20 acres property! It is situated on a ridge with a spectacular mountain view. Our house offers comfort & entertainment. The property will give you the full vacation in the woods experience. This is just what you need!

The Modern Lakehouse
This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

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.

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.

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 Winthrop house rentals
House rentals with a pool

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

the lake house

Farmhouse: Hot Tub, Mini Golf, Pickleball, POOL

There's No Place Like Home

Moose Pond Mountain Escape

Riverway Cottage

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

House in the woods
Weekly house rentals

Private Lake House, Firepit & Amazing Sunset Views

Hallowell Hilltop Home w/ Hot Tub, Sauna and AC

Mirror Pond Cottage

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!

Oak Leaf

Beautiful lake house on Tacoma Lakes near Coast

Veedon Fleece on the Lake

The Cottage at Red Top - Cozy Lakeside Year-Round
Private house rentals

July 7-14 Available: Large Porches & Living Space!

Lakeside Retreat

Lake front Retreat on Cobbosseecontee Lake

Perfect Maine retreat!

Mermaid's Chair | Private Beach | Hot Tub

Original "Moonlight Bay"

The Little Castle

Lakefront 4BR Home on Peninsula | Private Dock
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 918 | ﺩ.ﺇ 951 | ﺩ.ﺇ 786 | ﺩ.ﺇ 981 | ﺩ.ﺇ 907 | ﺩ.ﺇ 1,010 | ﺩ.ﺇ 977 | ﺩ.ﺇ 981 | ﺩ.ﺇ 881 | ﺩ.ﺇ 881 | ﺩ.ﺇ 841 | ﺩ.ﺇ 845 |
| Avg. temp | -6°C | -5°C | 0°C | 6°C | 12°C | 17°C | 21°C | 20°C | 16°C | 9°C | 3°C | -2°C |
Destinations to explore
- Montreal Vacation rentals
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- Quebec City Vacation rentals
- Portland Vacation rentals
- Mont-Tremblant Vacation rentals
- Newport Vacation rentals
- Providence Vacation rentals
- Bar Harbor Vacation rentals
- Salem Vacation rentals
- York County Vacation rentals
- Cambridge Vacation rentals
- The Hamptons Vacation rentals
- Sebago Lake
- Popham Beach, Phippsburg
- Sunday River Resort
- Willard Beach
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- East End Beach
- Pleasant Mountain Ski Area
- Popham Beach State Park
- Wolfe's Neck Woods State Park
- The Camden Snow Bowl
- Maine Maritime Museum
- Rockland Breakwater Light
- Portland Museum of Art
- Bradbury Mountain State Park
- Bug Light Park
- Reid State Park
- Grafton Notch State Park
- Farnsworth Art Museum
- Camden Hills State Park
- Mt. Abram
- Cellardoor Winery
- Maine Lighthouse Museum





