
House holiday rentals in Winthrop
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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!

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.

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.

The Nifty Village House
The Nifty Village House is an animal-free private home rental in the heart of Buckfield, Maine, a small New England town that sits on the Nezinscot River. This listing has been refurbished with a brand new kitchen, bathroom and laundry room. Conveniently located near Tilton's Market, Post Office, High School and more. We welcome guests with completed profiles, I.D. Verification, photo, and good reviews on Airbnb. The Nifty Village House is managed by Michael & Andrea at Niftybug Rentals.

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.

Riverside
Overlooking Kennebec River, Riverside is a perfect setting. Open 365 days per year; 2BR, 1 BA, kitchen, DR/common area. Situates 4 comfortably, 6 with the use of couches, 8 with added use of floor mattresses. Renovated, open concept, our home is wheelchair accessible. We accept Service dogs and will consider family dogs and other pets on a case-by-case; please ask. Owners reside on property in separate building. Outdoor trail cameras in use to monitor exterior of residence only.

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 .

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.

Hallowell Hilltop Home with 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, 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.

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

Treehouse Farm - Sebago

White Cap A-104 - Sunday River Condo

Epic Views, 9Mi SR, GameRm

Cozy Maine Church Retreat Near Portland • Fire Pit

Luxury Retreat | Dome, Spa & Breathtaking Views

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

The Getaway - A River Paradise

There's No Place Like Home
Weekly house rentals

Bluebird Cottage on Woodbury Pond

Cozy Sunshine Lake Cottage

The Berry Place

1790s Farmhouse on 16 Acres in Bowdoinham!

Manor Suite,cozy newly renovated,downtown & beach

The Wheel House, Richmond Maine

Cozy Wilton home.

Beautiful Maine Lakeside Cottage
Private house rentals

Stunning, private Maine lakefront home w/ hot tub.

The Little Castle

Lakefront Retreat in Augusta Cozy Holiday Cottage

Red Barn at The Appleton Retreat

Quaint Little Cottage

Waterfront Great Pond | Hot Tub | Trailer Parking

Sandy River Valley Farm House

Boothbay Harbor Bungalow
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
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- Waterfront rentals Winthrop
- Rentals with a kayak Winthrop
- Pet-friendly rentals Winthrop
- Rentals with a patio Winthrop
- Rentals with a firepit Winthrop
- Rentals with lake access Winthrop
- Rentals with outdoor seating Winthrop
- Rentals with a washing machine and dryer Winthrop
- Family-friendly rentals Winthrop
- House rentals Maine
- House rentals United States
- Sebago Lake
- Sunday River Resort
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- East End Beach
- Pemaquid Point Lighthouse
- Willard Beach
- Coastal Maine Botanical Gardens
- Wolfe's Neck Woods State Park
- Sunday River Golf Club
- The Camden Snow Bowl
- Maine Maritime Museum
- Bradbury Mountain State Park
- Portland Museum of Art
- Mt. Abram
- Farnsworth Art Museum
- Rockland Breakwater Light
- Pleasant Mountain Ski Area
- Cellardoor Winery
- East End Beach




