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Winthrop vacation rentals

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Top-rated vacation rentals in Winthrop

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

Apartment in Richmond
Designers Dream 1br Apt where class meets relax!!!
This Designers Dream 1br apartment is located in the quintessential small Maine town of Richmond. Open the door feast your eyes on this truly unique and beautiful spot and get ready to relax or explore! Richmond is home of Swan Island a great spot to explore via kayak or canoe or just grab the ferry! We're 45 min to all downtown Portland has to offer. We are an hour to Booth Bay Harbor and the beautiful botanical gardens. Popham beach is 45 min away, one of the most amazing beaches in state.
$70 per night
Loft in Hallowell
Loft apt w private hot tub/patio/shared entrance
The Widow Avery House is a historic Georgian Federal located within two blocks of downtown Hallowell. There is a spacious bedroom with two twin beds and desk with desktop computer available for use, a sitting area with couch and large roku TV, dining area with fridge, microwave, toaster oven and keurig with complimentary coffee and private bathroom with shower. During the season complimentary bikes and kayaks are available. If the guest has a service dog, the pet deposit is $1500.
$99 per night
Apartment in Winthrop
A little piece of heaven
Enjoy your stay in a fully furnished apt with lake access, very private setting, 1 hr east from the Rangeley area, 1 hr 15 min west from Boothbay Harbor. Enjoy your lunch sitting on a private deck overlooking Annabessacook lake.
$130 per night

Stay near Winthrop's top sights

Hannaford Supermarket37 locals recommend
FAST EDDIES DRIVE IN8 locals recommend
Lakeside Lodge And Marina3 locals recommend
Winthrop House of Pizza6 locals recommend
TJ's Pizzeria5 locals recommend
Peppers Garden & Grill6 locals recommend

Other great vacation rentals in Winthrop

Home in Lisbon
Unplug at a Beachy Bolthole with Classic New England Style
$65 per night
Apartment in Wilton
Single Room Suite near Downtown Wilton - UNIT#2
$43 per night
Apartment in Richmond
The Barn by Swan Island: Whimsical, Comfy, & Fun!
$71 per night
Guest suite in Lewiston
Sanctuary in the City
$127 per night
Cabin in Winthrop
Quaint & cozy cabin in beautiful wooded setting
$128 per night
Guest suite in Hallowell
Welcome to the Brown House! New Hallowell studio
$70 per night
Tiny home in Winthrop
Lakefront guest cottage,
$140 per night
Apartment in Hallowell
The Gallery
$145 per night
Apartment in Winthrop
Efficiency Apartment, The Loft
$100 per night
Guest suite in Monmouth
Welcome to The Nest - 1 bed, deck w/bath & parking
$100 per night
Apartment in Augusta
Apartment in Historic Neighborhood
$100 per night
Cabin in Readfield
Pet-Friendly Lakefront A-Frame
$250 per night

Quick stats about vacation rentals in Winthrop

Total rentals

60 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

40 properties are a good fit for families

Total number of reviews

1.4K reviews

Nightly prices starting at

$40 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Kennebec County
  5. Winthrop