
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.

Room B with private entrance, bathroom & hot tub
Room B is a small (10’ x 10’) but cozy room with full size bed with luxury mattress and private bathroom (5’ x8’) with towel warmer & glass shower. The room includes a desk, TV, minifridge, microwave, coffee maker, dresser, reading chair & private entrance. In the summer we have bicycles to use on the rail trail and kayaks for the Kennebec River. Year round hot tub. Downtown is just a block away where there are numerous restaurants and pubs with live music. Hiking trails & waterfalls nearby.

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.

Maine lakehouse-Ice fishing, skiing, snowmobiling
Beautiful lake living & winter activities, 2.5 hours from Boston, 40 min. from Portland. Near skiing- 1:20 from Sunday River, 1:10 Pleasant Mtn., 1:05 Mount Abram Ski Area, 0:20 Lost Valley. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances. Minutes to Lewiston/Auburn - close to dining and stores. Well known ice fishing spot , cross-country skiing nearby too. Fire pit, great sunsets.

Jill's Place!
This is a brand new daylight basement airbnb with access to Cobeeseecontee Lake in Winthrop Me. 2 bdrm. 1 with a queen and 2nd with 2 twins. It is decorated with with white shiplap, beautiful hardwood floors and very light and bright. It is 160 ft from the lakeside where there is a very nice grassy area with lounge chairs, a dock, and a swimming area. 1 kayak and a peddle lboat included. 500 ft away from the Travis Mills restaurant "The White duck" 2 miles from the famous Cabin Masters!

Cozy Cabin with Lake Access
This cozy cabin includes access to Lake Cobbossee, one of the most popular lakes in central Maine. It’s tucked away in a small private community where you can escape into peace and relaxation. The cabin is newly renovated and the yard is surrounded by trees, leaving you with plenty of privacy to roast s’mores and have cookouts with your family. It’s a short walk to the lake where you can drop in your kayak or throw a line out to one of the best fishing/recreational lakes in central Maine.

Welcome to the Brown House! Hallowell studio
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 15 minute drive to visit Maine Cabin Masters. Hour drive to Boothbay Harbor, Rockland, or Belfast. Studio is located above owners garage : separate entrance and off street parking. Included: linens, towels, TV, WiFi, single Keurig, microwave, toaster, college size dorm fridge, small cooler

Cozy, Efficiency Apartment with Hot Tub
Keep it simple at this peaceful, centrally-located efficiency apartment above our garage. 15 minutes to Gardiner/Augusta, 15 minutes to I95/295. Less than one hour from Portland. Sit by the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and play. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

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.

Floating Island Cabin Private Pet-Friendly Retreat
The Nautilus is a floating love letter to reinvention — a cabin, a tiny home, and a houseboat all rolled into one quietly wonderful idea. Moored beside 1 Big Sustainable Island, it lets you wake to gentle waves at your door, watch the sunrise from bed, and step straight onto a floating porch for morning coffee. It’s proof that with a little imagination (and a lot of care), something old can become something entirely new.

Downtown Augusta Studio - Newly Renovated #3
Located at the heart of downtown Augusta, this newly renovated studio apartment is a wonderful choice when visiting Augusta Maine! The apartment comes fully furnished with brand new furniture, supplies and bedding! The apartment has keyless entry via a keypad with each guests receiving a unique pin. There is parking and free laundry available on site. Enjoy a stylish experience at this centrally-located place.

The Barn by Swan Island: Whimsical, Comfy, & Fun!
Welcome to the place we call "The Barn by Swan Island." Located in Richmond, ME, just a short distance from the free boat launch to Swan Island in the Kennebec River. Originally built in the mid 1800's as an attached barn to our lovely Victorian home, we have completely renovated and remade the space into a fun, comfy, and whimsical AirBnB experience. An ideal location for a trip to Midcoast Maine!

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.
Popular amenities for Winthrop vacation rentals
Other great vacation rentals in Winthrop

Peaceful Private Room on the Nezinscot River

Charming waterfront camp on Maranacook Lake

Elegant Cobbossee Lake cottage with dock

WillowsAwake Winery Stay

Lake Front Cozy/Quiet 2 BR Home

Cozy cabin in a very fun and convenient location.

Private Suite at Historic Wilde Kind Farm

Harper Joy - A Tiny Home Experience
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $226 CAD | $246 CAD | $250 CAD | $250 CAD | $321 CAD | $323 CAD | $328 CAD | $342 CAD | $308 CAD | $304 CAD | $273 CAD | $279 CAD |
| Avg. temp | -6 °C | -5 °C | 0 °C | 6 °C | 12 °C | 17 °C | 21 °C | 20 °C | 16 °C | 9 °C | 3 °C | -2 °C |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Winthrop?
Four-legged friends are welcome in Winthrop. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Winthrop?
Yes! Work meets play with ease at over 30 vacation rentals in Winthrop featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly vacation rentals in Winthrop?
Winthrop has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cabin rentals in Winthrop?
Experience the best of Winthrop with our cabin rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cabin rentals in Winthrop have air conditioning?
Absolutely! We offer over 10 cabin rentals with air conditioning in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Winthrop have wifi?
Absolutely! We offer over 10 cabin rentals with wifi in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winthrop have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Winthrop. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cabin Rentals in Winthrop?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Winthrop

Total vacation rentals
Explore 70 vacation rentals in Winthrop

Nightly prices starting at
Winthrop vacation rentals start at $55 CAD per night before taxes and fees

Verified guest reviews
Over 2,170 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Winthrop vacation rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Winthrop rentals

4.9 Average rating
Winthrop stays are highly rated by guests—averaging 4.9 out of 5!
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- Sebago Lake
- Sunday River Resort
- Popham Beach, Phippsburg
- Popham Beach State Park
- Pemaquid Beach
- Willard Beach
- Pemaquid Point Lighthouse
- East End Beach
- 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
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- Pineland Farms
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- East End Beach




