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Vacation rentals with outdoor seating in Winthrop

Find and book unique accommodations with outdoor seating on Airbnb

Top-rated accommodations with outdoor seating in Winthrop

Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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Townhouse in Sabattus

4.85 out of 5 average rating, 149 reviews

Modern Victorian

This is a beautifully renovated, private, 2 bedroom, first floor of a duplex. The yard is fenced in and has a large deck. The unit is very light and bright and tastefully decorated. The rooms are very large and the kitchen is open to the living room. It is in a quaint little village with a little country store just steps away where you can find almish anything you need! 10 minutes from Bates College and many lakes. Hop on the highway and be in Portland in 40 minutes or the ocean in 45 minutes!

Oct. 10 – 17

$207 CAD per night

Guest favourite

Guesthouse in South Bristol

4.98 out of 5 average rating, 346 reviews

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Dec. 4 – 11

$247 CAD per night

Guest favourite

Guest suite in Monmouth

4.97 out of 5 average rating, 103 reviews

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.

Dec. 17 – 24

$196 CAD per night

Guest favourite

Home in West Paris

4.99 out of 5 average rating, 114 reviews

Four Season Western Maine Adventure Base

Make some memories at this family-friendly property. Enjoy panoramic views of Maine's western foothills. Owned by an outdoor-loving family, complete with hounds and chickens, this is a perfect spot to launch your Maine adventures. On the doorstep of skiing, hiking, biking, hunting, fishing, kayaking,canoeing. Enjoy beautiful sunrises and sunsets, sightings of eagles, moose, deer, sounds of peepers, woodcock, wild turkey gobbles and whip-o-wills. Enjoy the lifestyle that makes this Vacationland.

Oct. 31 – Nov. 7

$207 CAD per night

Guest favourite

Apartment in Woodstock

4.96 out of 5 average rating, 234 reviews

Ski, Swim, Hike, Bike, Repeat!

Come to a cozy mountain getaway nestled in the foothills of the Mahoosuc Range where the White Mountains complete the mise en scène and Mt Abram is prominent in the foreground. In winter, enjoy the hot tub or warmth of the greenhouse room after a day at Mt Abram or Sunday River, and in warmer months enjoy the shaded patio and the apartment's natural cooling. Many outdoor & dining destinations are within as few as ten minutes. If you want a more peaceful and slower pace in any season, stop by!

Aug. 19 – 26

$176 CAD per night

Guest favourite

Guesthouse in Harpswell

4.95 out of 5 average rating, 431 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, comfy, spacious, colorful and bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Two spectacular state parks with expansive beaches within a scenic 35 minute drive! Just 45 minutes (33 miles) to Coastal Maine Botanical Gardens! Saturday check-in may be available before mid June. Please message us.

Nov. 26 – Dec. 3

$205 CAD per night

Guest favourite

Home in Buckfield

4.91 out of 5 average rating, 154 reviews

The Nifty Village House

The Nifty Village House is an animal-free private home rental in the heart of Buckfield, Maine, a small New England town that sits on the Nezinscot River. This listing has been refurbished with a brand new kitchen, bathroom and laundry room. Conveniently located near Tilton's Market, Post Office, High School and more. We welcome guests with completed profiles, I.D. Verification, photo, and good reviews on Airbnb. The Nifty Village House is managed by Michael & Andrea at Niftybug Rentals.

Aug. 30 – Sep. 6

$179 CAD per night

Guest favourite

Loft in Hallowell

4.9 out of 5 average rating, 139 reviews

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.

Apr. 29 – May 6

$120 CAD per night

Guest favourite

Treehouse in Woodstock

4.99 out of 5 average rating, 152 reviews

Treehouse With Hot Tub Close to Sunday River!

This authentic, luxury treehouse was designed by B'Fer Roth, DIY Network TV host of The Treehouse Guys and built by the Treehouse Guys. Nestled in the woods on a quiet, private rd with no neighbors in sight, the treehouse is just 15 minutes to Sunday River Ski Resort, 5 minutes to Mt. Abram and 10 minutes to downtown Bethel. The treehouse is abutted by 626 acres of Bucks Ledge Community Forest (7 miles of hiking/snowshoeing trails accessible from the treehouse).

Mar. 2 – 9

$615 CAD per night

Guest favourite

Cottage in Sidney

4.91 out of 5 average rating, 101 reviews

Waterfront Cottage

The Waterfront Eagle Pine Cottage sits directly on Snow Pond, just 15 minutes from Colby College and downtown Waterville and 1/2 mile from the New England Music Camp. Enjoy the BEST sunset views from the private dock and listen to the waves and loons at night. The private front deck is the perfect spot for a sunset cocktail after a day of swimming and kayaking from the sandy beach. You also have an outdoor hot soaking tub and access to barrel sauna. Paradise!

Sep. 26 – Oct. 3

$596 CAD per night

Guest favourite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, and swim, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Dec. 10 – 17

$131 CAD per night

Guest favourite

Cabin in Litchfield

4.87 out of 5 average rating, 139 reviews

Blue Loon Camp on Pleasant Pond

This is a lovely cozy camp on Pleasant Pond. Public boat access makes it a popular lake for boating and bass fishing. The camp has dock and swim float for water fun and cool breezes from the lake make it a lovely place to be in the summer. Winter time the lake accommodates ice fishing and snowmobilers. The cabin sleeps four in bedrooms and two in the loft. Get away from it all with NO wifi or television to distract from the recreational activities.

May 12 – 17

$209 CAD per night

Vacation rentals for every style

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Popular amenities for Winthrop outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Guest favourite

Home in Appleton

4.96 out of 5 average rating, 123 reviews

The Barn

Oct. 30 – Nov. 6

$210 CAD per night

Guest favourite

Home in Waterville

4.79 out of 5 average rating, 146 reviews

Cozy House in Waterville

Apr. 9 – 16

$215 CAD per night

Guest favourite

Home in Edgecomb

4.95 out of 5 average rating, 405 reviews

Sheepscot Harbour Cottage/waterview

Jan. 22 – 29

$237 CAD per night

Guest favourite

Home in Farmington

4.98 out of 5 average rating, 166 reviews

Farmington. Walk to UMF & town. Family visits!

Sep. 10 – 17

$197 CAD per night

Guest favourite

Home in Canton

4.98 out of 5 average rating, 119 reviews

Private Lake House with Fire Pit and Sunset Views

Oct. 12 – 19

$560 CAD per night

Guest favourite

Home in Litchfield

4.92 out of 5 average rating, 114 reviews

Beautiful lake house on Tacoma Lakes near Coast

Sep. 9 – 16

$421 CAD per night

Guest favourite

Home in Freeport

4.99 out of 5 average rating, 163 reviews

"The Cozy Cottage in the heart of Freeport Village

Jan. 24 – 31

$211 CAD per night

Guest favourite

Home in Farmington

4.98 out of 5 average rating, 175 reviews

Old Ramsdell Farm

May 22 – 29

$196 CAD per night

Apartment rentals with outdoor seating

Guest favourite

Apartment in Damariscotta

4.92 out of 5 average rating, 255 reviews

Fernald's Backside

Jan. 8 – 15

$186 CAD per night

Guest favourite

Apartment in Damariscotta

4.94 out of 5 average rating, 339 reviews

Cottrill House on Damariscotta River # 1

Dec. 4 – 11

$168 CAD per night

Guest favourite

Apartment in Farmington

5.0 out of 5 average rating, 109 reviews

Powder House Hill Cottage Farmington, Maine

Aug. 23 – 30

$172 CAD per night

Guest favourite

Apartment in Rangeley

4.93 out of 5 average rating, 228 reviews

Brimwood Overlook Apartment

Apr. 27 – May 4

$203 CAD per night

Guest favourite

Apartment in Waterford

4.98 out of 5 average rating, 171 reviews

A+ Classy Convenient Accommodation, Western Maine

Jan. 6 – 13

$201 CAD per night

Guest favourite

Apartment in Bethel

4.97 out of 5 average rating, 189 reviews

Have you found YOUR Happy Space yet?

Oct. 16 – 23

$196 CAD per night

Guest favourite

Apartment in Damariscotta

4.84 out of 5 average rating, 461 reviews

"Ship Shape": waterfront, cozy studio- downtown

Nov. 8 – 15

$191 CAD per night

Guest favourite

Apartment in Topsham

4.87 out of 5 average rating, 498 reviews

Maine Stay with private hottub, near Brunswick

Oct. 17 – 24

$270 CAD per night

Condo rentals with outdoor seating

Guest favourite

Condo in Boothbay Harbor

4.91 out of 5 average rating, 22 reviews

Battered Buoy - Newly renovated, two bedroom condo

Nov. 8 – 15

$401 CAD per night

Guest favourite

Condo in Falmouth

4.95 out of 5 average rating, 42 reviews

Falmouth 3 Bedroom/2 Bath Loft Condo

Nov. 12 – 19

$730 CAD per night

Condo in Bath

4.84 out of 5 average rating, 98 reviews

Bowdoin, Lighthouses, Downtown, Beach, Sleeps 6

Jun. 5 – 12

$363 CAD per night

Guest favourite

Condo in Bethel

4.75 out of 5 average rating, 102 reviews

Sunday River Ski Area Condo, Bethel

Apr. 20 – 27

$279 CAD per night

Condo in Standish

4.86 out of 5 average rating, 14 reviews

Lakefront one bedroom condo with kitchen

Sep. 11 – 18

$290 CAD per night

Guest favourite

Condo in Newry

5.0 out of 5 average rating, 79 reviews

Private escape located in the mountains of Maine

Dec. 25 – Jan. 1

$359 CAD per night

Condo in Greenwood

4.71 out of 5 average rating, 7 reviews

Condo at Mt Abram-biking, skiing,golf & relaxation

Jul. 3 – 8

$247 CAD per night

Guest favourite

Condo in Bethel

4.97 out of 5 average rating, 36 reviews

3br Eden Ridge near Sunday River!!

Jan. 6 – 13

$655 CAD per night

Quick stats about vacation rentals with outdoor seating in Winthrop

Total rentals
30 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
740 reviews
Nightly prices starting at
$82 CAD before taxes and fees

Destinations to explore