Vacation rentals in Winthrop

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Top-rated vacation rentals in Winthrop

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Guest favourite

Cottage in Manchester

4.89 out of 5 average rating, 28 reviews

Lakefront cozy cottages w/ dock, canoe & fire-pit!

Situated a few steps from the water of Lake Cobbossee (Cobbosseecontee), with direct views of the sunset. So close to the lake it feels like you are on a boat. The cottage and bunkhouse are welcoming and very cozy. If you prefer a high-end lake house with lots of modern conveniences, this might not be for you, but it may be exactly what you need to relax and forget all your worries for a while. Curl up inside, hang out by the fire pit, swim off the dock or take the canoe out to spot some loons.

Top guest favourite

Island in Monmouth

4.99 out of 5 average rating, 195 reviews

Island Aframe Adventure in Maine

Discover how easy and relaxing secluded island life can be. Sleep comfortably. Cook your favorite meals. Chill out in a hammock. Bask in glow of the campfire. Listen to the loons call. Warm your cabin with a woodstove. Enjoy hot showers. Play on the rope swing. Canoe or kayak the lake. Go fishing. Explore the trails of a 14 acre wooded island. Enjoy super clean, Superhost, Maine Guide hospitality. We'll help you settle into the rhythm of island life and return you refreshed, renewed, and ins

Guest favourite

Home in Winthrop

5 out of 5 average rating, 15 reviews

Waterfront | Dock | Fire-pit | Laundry!

Spacious four-season lakefront camp on peaceful Dexter Pond in central ME. Enjoy great fishing, canoeing, stand-up paddle boarding, kayaking, or relax and watch the sunsets and loons from the large porch overlooking the pond. The home is in a great location close to Winthrop Center and Wayne (10 mins to local grocery store/ farmers market) 30 mins to Augusta/airport. Many hiking trails nearby and lots of other areas to explore. It's beautiful in all seasons. Private dock, firepit, and laundry!

Top guest favourite

Guest suite in Monmouth

4.98 out of 5 average rating, 163 reviews

Welcome to The Nest - 1 bed, deck w/bath & parking

Enjoy easy access to entertainment, restaurants & shopping. Historic Cumstom Theater, local Bakery, Bar & pizzeria. Willows Awake and The Vista wedding venues w/tasting rooms. Microbrewery’s Grateful Grains & Van der Brew tap rooms w/food trucks & entertainment. Maine turnpike access for shopping;Freeport LLBean, Portland, Bath, Augusta, Hallowell & Lew/Auburn areas. Tour Bates,Bowdoin, Colby, Thomas & Husson. Golfing, boating, antiques, State Parks, hiking/walking trails,beaches & Festivals.

Guest favourite

Home in Farmington

4.97 out of 5 average rating, 230 reviews

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.

Top guest favourite

Home in Hallowell

4.98 out of 5 average rating, 133 reviews

Hilltop Retreat with A/C, 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 or infrared sauna, 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.

Superhost

Cabin in Monmouth

4.86 out of 5 average rating, 36 reviews

The Woodland Lodge

Looking for a cozy family-friendly get away in the beautiful woods with access to a shared beach on Annabessacook Lake, look no further than The Woodland Lodge. Located in Monmouth ME, the cabin is close to the public boat launch for Cobbosseecontee Lake and Whittier Woods trails. It is 30 minutes to Augusta Regional airport, 1 hour to Portland Jetport, and 90 minutes to Sugarloaf. Enjoy the peaceful woods, shared beach access, and beautiful hiking trails nearby!

Top guest favourite

Apartment in Winthrop

4.72 out of 5 average rating, 18 reviews

Cozy Apartment with In-Town Convenience

This is a 2nd story apartment above our garage with a small but fully equipped kitchen, full-size refrigerator, microwave, electric stove/oven, double sink (no dishwasher), a plentiful supply of dishes, tableware, cookware, new queen bed, bathroom with shower, hair dryer, bathroom necessities, living area with couch/queen size futon, Smart TV with Apple TV, Fubo TV, wifi, iron & ironing board. Our preference is for long-term renters.

Top guest favourite

Cabin in Winthrop

4.97 out of 5 average rating, 71 reviews

Quaint & cozy cabin in beautiful wooded setting

Kick back and relax in this calm, stylish space. Less than 15 minutes to Augusta, and an hour from Portland! Close to many amenities, but far enough out to enjoy nature. The cabin sits on 33 acres, with fields and trails. The cabin itself has Wi-Fi, cable tv, a lofted queen bedroom, all of which have been recently updated. Outdoor amenities include BBQ grill, and lakes and ponds in close proximity.

Superhost

Home in Winthrop

5 out of 5 average rating, 3 reviews

Serene Lakeside Retreat

Relax with the family at this peaceful lakefront retreat on Cobbosseecontee Lake. Lovingly remodeled with care, this cozy 2-bedroom cottage blends Maine cabin charm with modern updates. Enjoy a full kitchen, spacious living area, two baths, a screened porch, and a deck with stunning lake views. Kayaks included! Unwind, explore, and make lifelong memories at this beautiful waterfront escape.

Superhost

Cottage in Winthrop

5 out of 5 average rating, 13 reviews

Little Landing Cottage | Lakefront · Dock · Kayaks

Cozy lakefront retreat with dock, kayaks, and sunsets. Walk to marina & restaurant. Pet-friendly and peaceful year-round. Slow down, breathe deep, and let the lake carry your worries away. This charming cottage invites you to reconnect—with nature, loved ones, and yourself. Perfect for couples, small families, or close friends seeking a cozy and quiet escape just steps from the water.

Guest favourite

Cabin in Winthrop

4.98 out of 5 average rating, 41 reviews

Lake Cabin in the Trees

Quiet lakefront cabin tucked in the woods with shimmering views of Wilson Pond below, the last house on a private dirt road. Dive in for a swim from the private dock or kayak to the lake's small islands. Stay connected with a dedicated office with desk and fast internet. A calm, secluded getaway for any season.