
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.

Off-Grid Escape. Wood Fired Hot Tub. 4 Kayaks
Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

The Nest at Camp Skoglund
Sitting 125 feet from the east shore of Echo Lake is the Nest at Camp Skoglund. A cozy cottage for two with all of the amenities you will need. Your deck provides a wooded view of the lake and we offer a fully equipped waterfront for your relaxation and fun on the water. A fire pit is also available. If you need lodging for more than 2, please inquire about our other cabin, Pop's (also on AirBnb). We are open seasonally starting in early June until Columbus Day or later depending on the weather.

Quiet Lakefront Home, Private Dock!
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!

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.

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!

Dreamy Post&Beam Hideaway Near Portland & Freeport
Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

The Cottage at Red Top - Cozy Lakeside Year-Round
The Cottage at 60 Red Top Drive is a cozy, family friendly place to enjoy quality Maine lake-time. You will have direct access to Anabessacook Lake including a sandy beach area. There is also ample yard space for relaxing and playing games. Indoors, the cottage has plenty of room for the family to be comfortable and a full kitchen. The cottage is a private space on its own, or can be rented in combination with The Main House for an extended family getaway! Ice fishing is right outside!

The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

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.

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.

SNOW SWEET, A Yurt for All Seasons
Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

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

Quiet Lake Front Cabin

Kirby Island Road Retreat

Private Hilltop View

Meadow Breeze cottage

A little piece of heaven

Country Charm, City Convenience

The Craic House Maine #mainethewaylifeshouldbe

The Cloud Cabin
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 4,086 ZAR | R 4,135 ZAR | R 2,730 ZAR | R 2,991 ZAR | R 3,841 ZAR | R 3,857 ZAR | R 3,923 ZAR | R 4,086 ZAR | R 3,678 ZAR | R 3,629 ZAR | R 3,269 ZAR | R 3,334 ZAR |
| 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 $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Winthrop have air conditioning?
Absolutely! We offer over 20 house 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 House Rentals in Winthrop?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wifi, over 20 homes with a bbq area, 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 R 981 ZAR per night before taxes and fees

Verified guest reviews
Over 2,110 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Winthrop vacation rentals include wi-fi 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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