
Vacation rentals with outdoor seating in Winthrop
Find and book unique outdoor seating rentals on Airbnb
Top-rated outdoor seating rentals in Winthrop
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

Privacy, River, Pond, A frame Hot Tub EPIC Views,
14 Acres Secluded A-frame nestled along Clean Crooked River, Hot tub with breathtaking VIEWS and world-class fishing. Swim in the river, private pond or explore hiking trails right from your door. Central AC - Gas Fireplace - Modern Kitchen. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Invite a private chef, florist or yoga teacher to fully unwind. Heated bath floors.

Cozy waterfront home on Merrymeeting Bay.
Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

Farm house, River, Island, animals & private Chef.
MARCH-APRIL DAILY. Medicine Hill is a 136 acre farm on the Sandy River complete with a swimming hole and an entire island to explore. We grow vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch unwinding and taking it all in. 4 private bedrooms have stunning views surrounded by trees or fields. And if the Chef is available..EAT!!!

Beautiful lakehouse 2.5 hours from Boston, 40 minutes from Portland
Beautiful lake living: 2.5 hours from Boston, 40 min. from Portland. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances, air conditioning. Minutes to Lewiston/Auburn - close to dining and stores. Spend your days swimming, canoeing, kayaking and fishing, use our grills or lobster pot to prepare your dinner and relax by the fire pit, toasting s'mores while watching the gorgeous sunsets.

Cozy 3-bedroom residential home on working farm
Ever wanted to chuck it all and buy a farm? We did in 2010 and now want to share it with you. The "Dell" sits at the entrance to Double Z Land & Livestock, a working farm owned and operated by The Abbruzzese family. Rolling hills, open fields, and grazing farm animals grace this 75-acre farm. If you want a glimpse of country life, seek to switch up your work-from-home routine, or just want to get away, come take up residence on the farm. If it's lambing season, you might even see some babies ;)

Beautiful lake house on Tacoma Lakes near Coast
Beautiful 4BR on Tacoma Lakes 50' from water, amazing views Screened in Porch w/peaceful views 3 spring fed lakes joined by 2 bridges Private dock Bring your boat or local company can rent/deliver motor boat Canoe/2 Kayaks Wifi/3 SmartTV/Alarm System FirePit, Gas Grille, Lawn Chairs Shuffleboard table Washer/Dryer Provided: linens/towels/soap/shampoo/detergent NO SMOKING-NO PETS-NO SHOES INSIDE (please) *Must sign separate water front liability waiver after booking No cameras inside or out

Writers Cabin in the Woods with Sauna!
Nestled in the woods and on Adams Pond with new wood fired sauna! The cabin feels totally hidden away but is less than 10 minutes to Bridgton and Naples, hiking, beaches and restaurants. The woods are beautiful and peaceful and the pond is just down a mossy path. Great for couples or a weekend away. Large deck with grill and outdoor shower, firepit. There is a shared dock on the pond for swimming, fishing, or just enjoying the view as well as a canoe and 2 kayaks, and a paddle board.

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.

Forest Cabin with Wall of Windows
Escape to our newly built 850 sq ft cabin in Midcoast Maine, a peaceful retreat nestled in a 30-acre forest. Perfect for up to 6 guests, this unique space features a stunning wall of windows with forest views, just a short drive from charming coastal towns and scenic parks. Wake up to the gentle morning sun cresting over the trees, relax and breathe deeper under a star-filled sky, and witness what all four seasons have to offer. Your serene getaway awaits!

Private Lake House, Firepit & Amazing Sunset Views
Spring & summer at Lakeshore Point, a private lakefront home on Canton Lake in Maine. Privately set at the end of a quiet lane, this updated modern retreat offers 200’ of pristine waterfront and your own private sandy shoreline. Swim, kayak, and paddleboard by day, then gather around the fire pit at sunset. Thoughtfully designed with a full kitchen, WiFi, and outdoor shower, it’s where family adventure meets relaxed lakeside New England charm.

The NEST Haven awaits you.
You found your ultimate relaxation spot, sandy beaches on Rock Haven Lake (only 800' from your front door) infrared Sauna (accessible through the secret door) , 3 person hot tub, outdoor (seasonal) shower, luscious king seize bed, 6' TIPI daybed, firepit, outdoor tipi swing, a balcony and deck to enjoy the peaceful neighborhood. Round shower and deep claw foot soaker tub. Enjoy, relax and let your soul ponder.
Popular amenities for Winthrop outdoor seating rentals
House rentals with outdoor seating

Waterfront Gem walkable to Restaurants!

Beautiful lake-side home close to Portland Maine

The Loons' Nest: Lakefront oasis w/ private dock

Riverside

Lakefront: Private Hot Tub, Sauna & Free Massages!

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

Lakefront Log Cabin on Pleasant Lake

Rustic Farmhouse at Oxbow Brewery
Apartment rentals with outdoor seating

Charming West End Hideaway. Private Parking

Fernald's Backside

Sophisticated Charm at an unbeatable price!

25 MIDDLE -Historic Village Apartment (Unit A)

Downtown Hideaway-Loft HotTub Modern Clean Private

Cottrill House on Damariscotta River #2

The perfect getaway - Camden/Rockport/Rockland

Harbor for Two
Condo rentals with outdoor seating

Charming, newly remodeled space atop Munjoy Hill.

Private escape located in the mountains of Maine

Home away from home cozy new Apartment in Oakland

Top Of The Line Stay!

Direct Ocean View on the Eastern Promenade

10 Bed! 8 Bedrm! Enormous! Walk to bars! Parking!

Slope Side | Ground floor | Hot Tub, Pool, Sauna

Sunday River Locke Mountain Ski In/ Ski Out Pool
Quick stats about vacation rentals with outdoor seating in Winthrop

Total vacation rentals
Explore 40 vacation rentals in Winthrop

Nightly prices starting at
Winthrop vacation rentals start at G$8,396 GYD per night before taxes and fees

Verified guest reviews
Over 1,250 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Winthrop vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winthrop rentals

4.9 Average rating
Winthrop stays are highly rated by guests—averaging 4.9 out of 5!
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- Pet-friendly rentals Winthrop
- Rentals with a fire pit Winthrop
- Family-friendly rentals Winthrop
- Rentals with a kayak Winthrop
- Rentals with lake access Winthrop
- Rentals with a washer and dryer Winthrop
- Waterfront rentals Winthrop
- House rentals Winthrop
- Rentals with a patio Winthrop
- Rentals with outdoor seating Kennebec County
- Rentals with outdoor seating Maine
- Rentals with outdoor seating United States
- Sebago Lake
- Sunday River Resort
- Popham Beach, Phippsburg
- Popham Beach State Park
- Pemaquid Beach
- Willard Beach
- Pemaquid Point Lighthouse
- East End Beach
- Coastal Maine Botanical Gardens
- Pleasant Mountain Ski Area
- Wolfe's Neck Woods State Park
- The Camden Snow Bowl
- Maine Maritime Museum
- Farnsworth Art Museum
- Bradbury Mountain State Park
- Mt. Abram
- Portland Museum of Art
- Rockland Breakwater Light
- Maine Mineral & Gem Museum
- Grafton Notch State Park
- Bug Light Park
- Sunday River
- Pineland Farms
- Maine Lighthouse Museum




