House holiday rentals in Winthrop

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 ;)

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.

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 Outlet Studio, Rustic Comfort w Fireplace

Conveniently and perfectly located! Our studio is in a private building on a quiet dead end street yet walking distance to L.L. Bean, Bow Street Market, Leon Gorman Park, restaurants, breweries, live music, outlet shops, Freeport Farmers Market, the Amtrak station and all that downtown Freeport has to offer. A short drive to Wolfe's Neck State Park, Bradbury Mountain State Park, Mast Landing Audubon Sanctuary, the Desert of Maine, Winslow Park, farm stands and the beautiful mid-coast coast.

Farmington! Walk to town! Holiday family visits!

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.

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.

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.

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.

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Moore's place

🇺🇸🏳️‍🌈Our place is good for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends (pets). Close to hiking, Sugarloaf, ME IT Snowmobile trails is .03 miles away,located between Farmington, Skowhegan, and Augusta If your looking for someone to take you on a hike, and or short kayaking trip, pontoon ride around Lake Wassookeag. moose head lake on a Saturday or Sunday , (with a fee) just let us know