
House holiday rentals in Winthrop
Find and book unique houses on Airbnb
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!

Four Season Western Maine Adventure Base
Make some memories at this family-friendly property. Enjoy panoramic views of Maine's western foothills. Owned by an outdoor-loving family, complete with hounds and chickens, this is a perfect spot to launch your Maine adventures. On the doorstep of skiing, hiking, biking, hunting, fishing, kayaking,canoeing. Enjoy beautiful sunrises and sunsets, sightings of eagles, moose, deer, sounds of peepers, woodcock, wild turkey gobbles and whip-o-wills. Enjoy the lifestyle that makes this Vacationland.

Cozy 3-bedroom residential home on working farm
Ever wanted to chuck it all and buy a farm? We did in 2010 and now want to share it with you. The "Dell" sits at the entrance to Double Z Land & Livestock, a working farm owned and operated by The Abbruzzese family. Rolling hills, open fields, and grazing farm animals grace this 75-acre farm. If you want a glimpse of country life, seek to switch up your work-from-home routine, or just want to get away, come take up residence on the farm. If it's lambing season, you might even see some babies ;)

Porky's Parsonage! 3 BR 1.5 bath Farm house. Cozy!
Relax with the whole family at this 3 bed, 1.5 bath farm house. Perfect spot for a quiet and fun family trip. 250 yards from the Whistle Stop Trail for snowmobiling, snowshoeing and x-country skiing. 30-45 minutes from 5 ski areas(Titcomb, Sugarloaf,Sun River, Black Mountain and Lost Valley) 100 yards from the Androscoggin River and 1/4 mile to where you can drop in a Kayak or canoe. Walk to a waterfall. Huge yard for family fun, parking etc! Ride your ATV/snow machine straight to trails!

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.

Farmington and UMF! Walk to town! Skiers welcomed!
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.

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 .

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit
Escape to Camp Sweden, an eco-friendly waterfront sanctuary in the foothills of the White Mountains. Paddle across the private pond, go for a hike in the Mountains nearby, or jump in the new outdoor panoramic barrel sauna and let your worries evaporate away. Enjoy a unique and rejuvenating experience that connects you to nature without sacrificing comfort. This retreat offers all-season enjoyment for nature lovers and outdoor enthusiasts alike. Experience Maine’s beauty today

Sunny 2-BR 5 min to Bates & River Trails
A classic 1920s Maine bungalow lovingly renovated. Our pet-friendly plant-filled home is an Auburn favorite. Unwind in our sunlit yoga studio - ideal for meditation, painting, or movement. Whisper-quiet heat-pump HVAC plus a hybrid water heater for eco-friendly comfort. Enjoy the rewilded pollinator garden of native Maine blooms. 5 min to Bates & St. Mary’s, 40 min to Portland, Brunswick, Bath, and Freeport. Stays of 14+ nights include complimentary weekly cleaning.

Private Lake House, Firepit & Amazing Sunset Views
Escape to Lakeshore Point, a winter wonder in Maine! This updated, modern lakehouse is nestled in the woods overlooking beautiful Canton Lake. Relax, unwind and recharge as you wake up surrounded by nature and incredible water views. With 200' of lakefront, you're just steps away from the lake with your own private sandy beach. Lakeshore Point is the last house on a private dirt road with all the amenities you're looking for- Full kitchen, wifi, outdoor shower and fire pit.

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.

1830s Cape hosted by George & Paul
This 1830 cape is for rent by the month or weekly or for a two-night minimum stay. It is located at the edge of the historic village of Waldoboro. It offers a convenient base to sightseeing in midcoast Maine. It’s old-fashioned, decorated with plants, antiques and paintings and features a large, fully equipped kitchen, music room with piano, television room with pull-out sofa, full bath with stall shower and outside patio. Your hosts are right across the driveway.
Popular amenities for house rentals in Winthrop
House rentals with a pool

Faith Lane with community pool

Sunday River Ski in/Ski Out Condo- White Cap A-307

Luxe Liberty: Getaway with Heated Indoor Pool!

Farmhouse: Ice Rink | Movie Cave | Hot Tub

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

The Getaway - A River Paradise

There's No Place Like Home

Privacy, River, Pond, A frame Hot Tub EPIC Views,
Weekly house rentals

2 Acre Waterfront w/Canoes & Kayaks, Game Room

The Berry Place

The Cottage at Red Top - Cozy Lakeside Year-Round

Cozy Wilton home.

Mountain House near Sunday River & Bethel Village

Beautiful Maine Lakeside Cottage

Quiet Lakefront Home, Private Dock, Laundry!

Lakefront 3 bedroom pet friendly on Messalonski
Private house rentals

The Little Castle

Bluebird Cottage on Woodbury Pond

Lakefront Retreat in Augusta Cozy Getaway

1790s Farmhouse on 16 Acres in Bowdoinham!

The Maine Oasis - Pondfront Home with Sunset Views

Peaceful Lakefront Getaway W/ Sunset Views & Dock

Red Barn at The Appleton Retreat

Cozy Lakefront Cabin-Private Dock-Kayaks-Firepit
Quick stats about house rentals in Winthrop

Total holiday rentals
Explore 30 holiday rentals in Winthrop

Nightly prices starting at
Winthrop holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 880 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Winthrop holiday rentals include wifi 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!
Destinations to explore
- Long Island Holiday rentals
- Boston Holiday rentals
- Hudson Valley Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Laurentides Holiday rentals
- Quebec City Area Holiday rentals
- Mont-Tremblant Holiday rentals
- Laval Holiday rentals
- Québec Holiday rentals
- Rentals with lake access Winthrop
- Family-friendly rentals Winthrop
- Rentals with a kayak Winthrop
- Rentals with a patio Winthrop
- Pet-friendly rentals Winthrop
- Waterfront rentals Winthrop
- Rentals with outdoor seating Winthrop
- Rentals with a firepit Winthrop
- Rentals with a washing machine and dryer Winthrop
- House rentals Maine
- House rentals United States
- Sebago Lake
- Sunday River Resort
- Popham Beach, Phippsburg
- Popham Beach State Park
- Pemaquid Beach
- Willard Beach
- East End Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- The Camden Snow Bowl
- Wolfe's Neck Woods State Park
- Pleasant Mountain Ski Area
- Maine Maritime Museum
- Farnsworth Art Museum
- Bradbury Mountain State Park
- Mt. Abram
- Portland Museum of Art
- Maine Mineral & Gem Museum
- Grafton Notch State Park
- Rockland Breakwater Light
- Sunday River
- Bug Light Park
- Pineland Farms
- East End Beach




