Vacation rentals in Winthrop

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Top-rated vacation rentals in Winthrop

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Guest suite in Monmouth

4.97 out of 5 average rating, 103 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.

Jan. 4 – 11

$189 CAD per night

Guest favourite

Loft in West Gardiner

4.98 out of 5 average rating, 112 reviews

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment. 15 minutes to Gardiner and Augusta, 15 minutes to I95/295. Less than one hour from Portland. Walk along the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to paddle in a kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and pay or twin air mattress. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Feb. 19 – 26

$190 CAD per night

Guest favourite

Guest suite in Hallowell

5.0 out of 5 average rating, 53 reviews

Welcome to the Brown House! Hallowell studio

Come and enjoy Hallowell and Central Maine while staying at our studio apartment. An easy walk to downtown Hallowell to shops, restaurants , and pubs. Take a walk on the Kennebec Rail Trail. A 10 minute drive to visit Maine Cabin Masters. Studio is located above owners garage with separate entrance and off street parking. Included: linens, towels, TV, WiFi, single Keurig coffee maker, microwave, toaster, college dorm size fridge

Feb. 2 – 9

$118 CAD per night

Guest favourite

Cabin in Litchfield

4.82 out of 5 average rating, 148 reviews

Cobbossee log cabin / post & beam

Come and enjoy this unique log cabin / post&beam just minutes walk from cobbossee stream. A wonderful place which can be enjoyed during any season, in the winter enjoy ice fishing on pleasant pond 10 minutes away, Cobbossoconte lake 20 min. or take an hours drive to the slopes to do some skiing. During the summer come enjoy the lakes and the slower pace of life, bike or run the country roads. There is a wood burning fireplace and stove, but firewood is not provided.

Sep. 24 – Oct. 1

$232 CAD per night

Guest favourite

Apartment in Hallowell

4.98 out of 5 average rating, 301 reviews

Two Bedroom Mid Century Modern Downtown Apartment

Experience this amazing two bedroom Mid-Century Modern apartment in Downtown Hallowell. This is newly renovated & steps away from a variety of restaurants & pubs. It has all the fun and funky charm of the early 1960’s with bright colors, rich woods, clean lines & shag rugs. All the modern comforts including stainless steel appliances, vessel sinks, soaker tub & new beds. A couple miles from the State Capital and centrally located between Brunswick and Waterville.

Nov. 10 – 17

$210 CAD per night

Superhost

Apartment in Winthrop

4.83 out of 5 average rating, 6 reviews

Jill's Place

This is a brand new daylight basement airbnb with access to Cobeeseecontee Lake in East Winthrop Maine. Note: this is not lakeside, but 1 house back and with l good views. It is 160 ft from the lakeside where there is a very nice grassy area with lounge chairs, a dock, and a swimming area. There is even a mooring for your boat! 1 kayak and a peddle boat included. 500 ft away from the fabulous White Duck Restaurant and lakeside marina where you can rent a boat.

Sep. 25 – Oct. 2

$250 CAD per night

Guest favourite

Cabin in Litchfield

4.87 out of 5 average rating, 139 reviews

Blue Loon Camp on Pleasant Pond

This is a lovely cozy camp on Pleasant Pond. Public boat access makes it a popular lake for boating and bass fishing. The camp has dock and swim float for water fun and cool breezes from the lake make it a lovely place to be in the summer. Winter time the lake accommodates ice fishing and snowmobilers. The cabin sleeps four in bedrooms and two in the loft. Get away from it all with NO wifi or television to distract from the recreational activities.

May 8 – 15

$183 CAD per night

Guest favourite

Home in Lewiston

4.99 out of 5 average rating, 138 reviews

Clean and comfortable home

First floor of newly renovated, well-stocked, single-family home in quiet, safe neighborhood. Full kitchen, 2 bedrooms each with comfortable queen-sized bed, full bathroom, on-site laundry. Shoppable art on-site :) Located less than 1 mi from Bates College and St. Mary’s Hospital. Less than 2 mi from Central Maine Medical Center. Proof of Covid-19 vaccination may be requested for all eligible to receive vaccine (including children).

Jun. 9 – 16

$191 CAD per night

Guest favourite

Tiny homes in Winthrop

5.0 out of 5 average rating, 18 reviews

Lakefront guest cottage,

This lakefront cabin is quiet and peaceful. The lake is beautiful with all types of wildlife. Kayaking, canoeing is available or you can just sit by the fire and enjoy the beautiful Maine woods. Use of kayaks, canoes, fire pit, gas grill, and dock slip for your own boat included. Our Tiny-house has everything you need for the perfect getaway. We provide you with linens, a stocked kitchen and a gas stove. Included wifi, and smart TV.

Jul. 9 – 16

$253 CAD per night

Guest favourite

Guesthouse in Richmond

4.9 out of 5 average rating, 137 reviews

The Studio

Welcome to our 2.5 acre haven! This studio is full of life with color that will bring your spirits up. It is a little over 400 sq. ft. with your own private entrance from the garage and above apartment, on the first floor, your own parking and not too far from the city. Richmond is a small town that sits near the Kennebec River and Swan Island where you can enjoy outdoor adventures. * Space not equipped for children *

Dec. 8 – 15

$158 CAD per night

Guest favourite

Cottage in Winthrop

4.98 out of 5 average rating, 49 reviews

Family friendly, 2-Bedroom cottage with lakeview

Enjoy your stay at The Coop, a brand new family-friendly, 2-bedroom cozy, modern cottage packed with amenities, nestled in the village of a rural town w/ lake views. There is a large yard with fire pit, snowmobile & walking trail access out back. A 10 minute walk to the beach & boat launch on Maranacook lake, as well as multiple local eateries and shops. Interested in a massage? Studio located below condo!

Nov. 10 – 17

$316 CAD per night

Guest favourite

Cabin in Winthrop

4.97 out of 5 average rating, 36 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.

Feb. 21 – 28

$204 CAD per night