Best Vacation Homes in Winthrop
House
10.0(32 Reviews)
2 Bedrooms
1 Bath
100 Guests
2000 ft²
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $292/Night
7 Nights - US $2,042
House
10.0(5 Reviews)
1 Bedroom
1 Bath
4 Guests
828.82 ft²
- Fireplace/Heating
- View
Pet Friendly
Parking
US $393/Night
7 Nights - US $2,751
House
10.0(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Kitchen
US $754/Night
7 Nights - US $5,278
Cabin
10.0(25 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $249/Night
7 Nights - US $1,743
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
904.17 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $550/Night
7 Nights - US $3,852
House
10.0(21 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $346/Night
7 Nights - US $2,423
Cottage
10.0(13 Reviews)
2 Bedrooms
1 Bath
5 Guests
744 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $669/Night
7 Nights - US $4,684
Cabin
10.0(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
Oceanfront- Ocean View
- Balcony/Terrace
- View
US $237/Night
7 Nights - US $1,658
Winthrop Luxury Rentals
House
1 Bedroom
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Air Conditioner
US $1,059/Night
7 Nights - US $7,412
House
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $952/Night
7 Nights - US $6,661
House
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $939/Night
7 Nights - US $6,572
House
10.0(9 Reviews)
5 Bedrooms
4 Baths
15 Guests
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $854/Night
7 Nights - US $5,977
House
9.5(2 Reviews)
1 Bedroom
2 Baths
8 Guests
1732.99 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
Child Friendly
US $676/Night
7 Nights - US $4,731
Cabin
9.8(10 Reviews)
1 Bedroom
1 Bath
4 Guests
834 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $563/Night
7 Nights - US $3,942
Apartment
7.6(4 Reviews)
1 Bedroom
1 Bath
8 Guests
600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $547/Night
7 Nights - US $3,832
New
House
4 Bedrooms
2 Baths
8 Guests
1728 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $539/Night
7 Nights - US $3,773
Winthrop Pet Friendly Vacation Rentals
Cabin
9.8(29 Reviews)
2 Bedrooms
1 Bath
8 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $387/Night
7 Nights - US $2,706
House
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
1001.04 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
Internet
US $335/Night
7 Nights - US $2,345
Cottage
9.8(22 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $281/Night
7 Nights - US $1,964
House
2 Bedrooms
1 Bath
4 Guests
2002.09 ft²
Private Beach- Oceanfront
- Fireplace/Heating
- Ocean View
US $194/Night
7 Nights - US $1,358
Cabin
9.6(4 Reviews)
2 Bedrooms
1 Bath
3 Guests
700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $185/Night
7 Nights - US $1,297
Apartment
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $215/Night
7 Nights - US $1,503
House
10.0(87 Reviews)
3 Bedrooms
2 Baths
10 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $305/Night
7 Nights - US $2,136
House
10.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
1880 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $339/Night
7 Nights - US $2,370
Winthrop Large Vacation Homes
House
9.6(5 Reviews)
5 Bedrooms
2 Baths
10 Guests
2688 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $490/Night
7 Nights - US $3,431
Villa
3 Bedrooms
2 Baths
8 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $433/Night
7 Nights - US $3,031
House
3 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $378/Night
7 Nights - US $2,648
Other
10.0(19 Reviews)
6 Bedrooms
2 Baths
12 Guests
3300 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $722/Night
7 Nights - US $5,055
House
4.6(14 Reviews)
4 Bedrooms
4 Baths
10 Guests
3048 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
US $618/Night
7 Nights - US $4,326
US $509/Night
7 Nights - US $3,563
Why Choose Rent By Owner for your Winthrop Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Winthrop
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can greatly enhance your experience, as the best seasons to enjoy the region's natural beauty and local activities often depend on what kind of vacation you’re seeking.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and longer daylight hours, making this the perfect time to indulge in outdoor activities around the area.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
The fall season offers vibrant foliage and mild temperatures, creating a picturesque setting for exploring and relaxing in your vacation rentals here.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
In winter, the region transforms into a snowy retreat, ideal for cozying up in comfortable vacation rentals while enjoying cold-weather charm.
Average Temperature Daytime: 25°F to 35°F - Nighttime: 10°F to 20°F
Spring (March to May)
Spring unveils a quieter atmosphere with blooming nature, offering a peaceful experience as you plan your stay in this destination’s rental options.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Winthrop
How to Book Your Winthrop Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Winthrop
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor grilling with a private barbecue area for memorable cookouts.
- Take advantage of spacious patios or decks perfect for relaxing and soaking in the scenic views.
- Explore nearby hiking or walking trails directly from your rental, immersing yourself in the area's natural beauty.
- Benefit from access to a fire pit for cozy evenings under the stars.
- Make use of outdoor seating areas designed for family gatherings or socializing with friends.
- Experience seasonal activities such as snowshoeing or cross-country skiing during winter months.
- Utilize well-maintained outdoor parking facilities to conveniently explore the region's outdoor attractions.
Top Attractions Around Winthrop
What attractions are nearby?
Nearby, you can enjoy a variety of outdoor activities such as boating, fishing, and hiking, making this destination perfect for those looking to explore the natural beauty of Maine’s scenic landscapes.
Family Activities
- Winthrop Historical Museum: Explore local history and enjoy engaging exhibits perfect for a family day in this part of Maine.
- Lake Shore Park: Spend quality time outdoors by the water, where you can picnic, play, or take a relaxing walk along the shoreline.
- Winthrop Recreation Area: Take advantage of hiking trails and open green spaces designed for outdoor fun suitable for all ages in this scenic region.
- Local Artisan Shops and Markets: Discover unique crafts and fresh local produce that offer a delightful family shopping experience here in the area.
Adult Activities
- Boating and Fishing on Androscoggin Lake: Enjoy a relaxing day on the water, where you can fish or rent a boat to explore the scenic surroundings of this popular regional destination.
- Exploring Local Trails and Parks: Discover the region’s natural beauty by hiking or biking along well-maintained trails that showcase the area's forests and lakes.
- Golfing at Nearby Courses: Tee off at some of the area’s top golf courses, offering picturesque views and a chance to practice your swing in an inviting setting.
- Dining at Local Restaurants: Savor authentic cuisine at local eateries that highlight regional flavors, perfect for unwinding after outdoor adventures here.
Other Places to Stay in Winthrop, ME
Wilson Pond
Annabessacook Lake
Maranacook Lake
Winthrop Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Outdoor Adventures: Take advantage of the scenic natural surroundings by exploring local parks and trails to fully enjoy the region's outdoor beauty.
- Visit Seasonal Events: Check out seasonal festivals or markets that highlight the area's local culture and provide authentic experiences during your stay.
- Discover Local Cuisine: Savor regional flavors by visiting nearby eateries, offering a taste of the region’s culinary specialties right at your doorstep.
- Choose a Convenient Location: Book a vacation rental close to key attractions and amenities for easy access and more time to relax and explore here.
Transportation Options
- Winthrop Transportation Services: Local transportation options include reliable shuttle and taxi services that connect you to key destinations around the area.
- Public Transit: The region offers bus routes that make it easy for you to explore nearby towns and attractions without the need for a personal vehicle.
- Car Rentals: Numerous car rental agencies in Winthrop provide convenient access to a variety of vehicles, giving you flexibility during your stay here.
- Biking and Pedestrian Paths: Well-maintained bike trails and pedestrian-friendly streets allow you to enjoy the scenic beauty of this destination at your own pace.
Local Customs Options
- Local Fishing Traditions: Engaging in or observing the region’s fishing practices offers insight into the community's historical reliance on water-based livelihoods.
- Seasonal Festivals: Participating in seasonal events celebrates the area's rich heritage and provides a chance to connect with local residents.
- Community Gatherings: Local gatherings often center around shared interests such as outdoor activities, fostering a welcoming atmosphere for visitors.
- Historical Preservation Practices: Respecting efforts to preserve historical sites in the area allows you to appreciate the region’s cultural identity and history.
Winthrop Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Winthrop?
There are a lot of options in Winthrop. If you plan on staying in the Winthrop area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winthrop:
- Discover your retreat - 3-bedroom cottage in Winthrop
- Rustic, peaceful lake house on Lake Cobbosseecontee; free WIFI, ADA friendly.
- Peaceful Fisherman's Paradise w/Deck + Fire Pit!
- Escape to our cozy Winthrop cabin on Dexter Pond
- Enjoy Sunset views on tranquil Dexter Pond
- Cozy Keyes Cottage | Lakefront Dock Kayaks
- Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
- ANNABESSACOOK WATERFRONT WITH DOCK
- Cozy Cabin on Cobbossee Lake near Lakeside Marina
- Little Landing Cottage On Cobbossee Lake
2. Which vacation homes in Winthrop are best for families?
If you are looking for a family-friendly vacation home in Winthrop, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winthrop:
3. How many Rentbyowner vacation rentals are available in Winthrop?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 63 in the Winthrop area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winthrop.
4. What is the cancellation policy for vacation rentals in this region?
Cancellation policies vary by property, and details are provided on each listing. You are encouraged to review the specific rental's terms or contact the owner directly for clarification.
5. How do I ensure my booking in Winthrop, Maine, is secure?
Bookings are secured through a trusted platform that offers secure payment options. To confirm your reservation, follow the instructions provided after selecting your preferred property and communicate with the owner if needed.
6. Are there any additional fees associated with my stay?
Additional fees such as cleaning, service charges, or taxes are specified on the listing page. Be sure to read all the details before completing your booking to avoid surprises.
7. Can I modify or cancel my reservation if plans change?
Modification and cancellation policies depend on the individual property owner’s terms. Refer to the listing details or contact the owner directly for information about making changes to your reservation.
8. What amenities can I expect when staying in a vacation rental in this area?
Amenities vary by property but often include essentials like Wi-Fi, full kitchens, and outdoor spaces. For specific amenities, review the property listing or reach out to the owner for confirmation.
