What are the top rated Cottage 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 Cottage Rentals in Winthrop: <a href="/property/rustic-peaceful-lake-house-on-lake-cobbosseecontee-free-wifi-ada-friendly/HA-1217940104" class="class="static-page-link"">Rustic, peaceful lake house on Lake Cobbosseecontee; free WIFI, ADA friendly.</a> <a href="/property/peaceful-fisherman-s-paradise-w-deck-fire-pit/HA-1214616353" class="class="static-page-link"">Peaceful Fisherman&#39;s Paradise w/Deck + Fire Pit!</a> <a href="/property/escape-to-our-cozy-winthrop-cabin-on-dexter-pond/HA-3213829435" class="class="static-page-link"">Escape to our cozy Winthrop cabin on Dexter Pond</a> <a href="/property/enjoy-sunset-views-on-tranquil-dexter-pond/HA-1214938063" class="class="static-page-link"">Enjoy Sunset views on tranquil Dexter Pond</a> <a href="/property/pet-friendly-family-homestead-1-hr-from-the-coast/HA-3213287619" class="class="static-page-link"">Pet friendly, Family Homestead 1 hr from the coast!</a> <a href="/property/spacious-5-bedroom-lakefront-home-on-pristine-lower-narrows-pond-in-winthrop/HA-3214416198" class="class="static-page-link"">Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop</a> <a href="/property/annabessacook-waterfront-with-dock/HA-3213400140" class="class="static-page-link"">ANNABESSACOOK WATERFRONT WITH DOCK</a> <a href="/property/cozy-cabin-on-cobbossee-lake-near-lakeside-marina/HA-3212848087" class="class="static-page-link"">Cozy Cabin on Cobbossee Lake near Lakeside Marina</a> <a href="/property/new-construction-2-br-apt-walking-distance-to-the-barn-at-silver-oaks-winthrop/HA-3214483548" class="class="static-page-link"">NEW Construction! 2-BR Apt walking distance to The Barn at Silver Oaks, Winthrop</a> <a href="/property/lakefront-cottage-sleeps-6-2-baths/HA-3213178026" class="class="static-page-link"">Lakefront Cottage - sleeps 6 - 2 baths</a>

How much does it cost to rent a cottage in Winthrop?

The average cost for a cottage rental in Winthrop is $400 per night. Visittheus has a wide list of great cottages near Winthrop that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Winthrop that allow pets?

Yes, here are the top cottage rentals in Winthrop that allow you to bring your pet: Discover your retreat - 3-bedroom cottage in Winthrop Little Landing Cottage On Cobbossee Lake Cozy Keyes Cottage | Lakefront Dock Kayaks Cozy Keyes Cottage Peaceful Fisherman's Paradise w/Deck + Fire Pit! Life on the Lake with Private Dock and Fire Pit! Little Landing Cottage-gorgeous View BBQ Wi-fi Escape to our cozy Winthrop cabin on Dexter Pond <a href="/all/usa/maine/winthrop" class="class="static-page-link"">See all pet-friendly vacation rentals in Winthrop on Visittheus</a>

Do you have any rental cottages in Winthrop that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Winthrop to find one that works for you.

Are there quality cottages in Winthrop that have indoor swimming pools?

As of 2026, the data from Visittheus shows that there are Over 10 private swimming pools or cottages with indoor pools in the Winthrop area along with other great amenities.

Winthrop Cottage Rentals By Owner

Discover your retreat - 3-bedroom cottage in Winthrop

From US $223

10.0 (176 Reviews)

Cottage

Discover your retreat - 3-bedroom cottage in Winthrop

Air Conditioner
Parking
TV

Winthrop Cottage Rentals & Holiday Homes

Find the best cottages in Winthrop - We found 10 exact matches

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