
Vacation rentals with outdoor seating in Winthrop
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Top-rated outdoor seating rentals in Winthrop
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Popular amenities for Winthrop outdoor seating rentals
House rentals with outdoor seating

Charming Coastal Home
We were remodeling our home and needed a place to stay for over a month and this place did not disappoint. The home is welcoming and super clean and neat. There were plenty of amenities for cooking and it was well stocked with paper products and a few toiletries as well as plenty of linens. It is so close to many great businesses and walkable to an excellent Gluten free bakery. The host was extremely kind and responsive to our needs- my son (7) said this home felt just like our own home. His favorite part was the “fancy fridge” that we could play music on and see different pictures according to the weather haha. Definitely a great place.

By the Sea - sleeps 11! Walk to beach
The accommodation is located in a quiet area and a short distance from the beach. I highly recommend this affordable place for a stay in Old Orchard Beach!

Spring into the season eating lobsters w/friends
Very nice place to stay big nice and clean recommended this place to everyone looking for a good place big and clean this the right place

Northern Solace
He has everything needed to make it comfortable!

LUX Designer Private Waterfront
Jon’s space was very clean, private, and presented a “wow” factor in every direction I turned. Very well thought out; a truly transformative experience!

Riverside
We had an amazing time over valentines day weekend. There was a snow storm and Kent snow blowed around our vehicle to make sure we could get out. The house is very comfortable and peaceful, amazing view of the river and just off the road enough to not be bothered by passing traffic. Definitely recommend!!!!

Waterfront Farmhouse with Modern Flair!
The home was very welcoming and accommodating for our family of 5. The views were spectacular at sunrise, sunset and during the snowstorm. Bald Eagles and hawks would land in the trees right in front of the house. Also, there was a skating pond down the street my family love to visit almost each evening. There was an alarm going off as soon as we arrived, Debbi was incredibly fast responding and sending someone to check it out clear it up. On the plus someone came and plowed the driveway after the snowstorm it was great. She left a basket of local food and my family ate it up. We are so thankful for our relaxing week and would love to return.

Lovely, relax and cozy home!
We’ve stayed a lot of places in the area and we will be booking this one again! Very clean, spacious, convenient. We did wish there was a full size pool table! But everything was really nice and we can’t wait to book again for our next ATV adventures!
Apartment rentals with outdoor seating

Bright & Sunny Apartment with Patio
Great spot for solo traveler or traveling duo! Convenient to lots of walkable spots. Easy parking. This place really isn’t for the tall of stature, but that’s spelled out fairly clearly in the listing. Very cozy!

Sophisticated Charm at an unbeatable price!
The apartment was just as described by the host, and was very comfortable for a two night stay, for two couples. Excellent, proactive, communication by the host prior to check-in. Very clear instructions. The kitchen was well equipped for breakfast (which is the only meal we ate at the apartment during our stay). A serrated knife would be a nice addition. All of the appliances were very clean, and in good working order. Entry to the building was easy. Be comfortable climbing stairs. Five minute drive, or 15 minute walk to downtown. Quiet and peaceful neighborhood. Would definitely return, and recommended it to others. Thank you for a nice stay, Susan.

Cape Elizabeth Garden Apt+Beach+Close to Portland!
My sister and I had a great stay at David and Kate’s place . Everything we needed was right at our fingertips and the bed was SO comfortable we wanted to take it with us ! Beautiful surroundings and easy to get everywhere ! Thank you David and Kate for sharing your place with us . Hope to visit again !

Sunny West End Apartment With Private Courtyard
Delightful place to stay in Portlands West end. It is easy walking distance to everywhere…. downtown and even the East side. Great restaurants in the neighborhood from breakfast to dinner. The apartment was immaculate and was stocked with just about everything you’d need. The shared yard was charming and felt very private. We have family in the area and I hope we can stay there again and again. It was much more comfortable than a B & B. Lorie was very responsive to anything you might need.

Comfy, Convenient Studio Apartment Near Downtown
Not only is Nicole a gracious host and cheerily responsive to questions, the space is adorable! Everything you need to be comfortable, in a great neighborhood, within walking distance to EVERYTHING downtown, including a very sweet harbor! 🌟🌟🌟🌟🌟🌟🌟🌟🌟🌟🌟🌟

The Brew House - 2nd Floor Private Apartment
Great apartment in a very walkable part of Portland, a perfect location for exploring the city. It was clean & spacious with a very comfortable bed and we appreciated the off-street parking. The owner Jeff and his wife are very friendly and served us a fantastic meal at their small brewpub downstairs. I normally wouldn’t choose a rental above a pub, but theirs closes at 9pm every night, so noise wasn’t an issue at all. Would highly recommended this unit for a stay in Portland.

Farnham Point Retreat
The place was amazing, such a great find! The hosts laid out check-in and check-out instructions very clearly and offered an abundance of amenities to make our stay more enjoyable. They offered toiletries, tide pods, cooking spices, coffee, books- the list could really go on and on. It really felt like a home away from home! Thank you to our wonderful hosts, we hope to visit again!!

Spacious 1st floor New England charm.
There's so much that can be said about this place and the area. We stayed for a week and barely scratched the surface of what's available to do. Within 15-20 minutes of driving, you'll find both sand and rocky waterfronts to explore, Island ferries, forest hiking, and countless amazing restaurants. Coming back to this place after each day of exploring felt like coming home to rest and recharge for the next day. Comfortable places to sit/sleep, conveniently supplied snacks, and great material to review what to put on your list for the next day. Please take my advice and stay here if you want to have a peaceful and fruitful stay in the Portland, ME area.
Condo rentals with outdoor seating

Cozy condo with North Conway at your finger tips!
Great place close to North Conway, clean, would happily stay there again!

Across from Storyland & in the Heart of the Mtns
Highly recommend a stay at Michelle and Jason’s place! It’s a great “home base” for whatever you’re looking to do, whether that be hiking, climbing, skiing, shopping, or exploring any of the charming towns nearby! Michelle and Jason were kind and communicative and their place is so adorable and comfortable! Great stay!

Cozy, clean, 2nd floor condo in Conway, NH!
A beautiful condo, just 20 minutes away from the heart of North Conway. Everything was in pristine condition and it is always amazing to have a kitchen at our fingertips. Beautiful views of the woods out back. Would definitely recommend to those coming to visit the North Conway, New Hampshire area and surroundings!!!!

Sunday River Locke Mountain Ski In/ Ski Out Pool
Great stay at Stephanie’s place - super easy ski on and off location! Cozy and functional first floor unit. Kids loved having access to the outdoor pool!

Rustic Willard Beach condo ten mins from Old Port!
What a wonderful place in a lovely neighborhood. The condo exceeded our expectations—it was even more beautiful in person. We had a comfortable, happy stay with our small children. Scratch Bakery and an ice cream parlor are right across the street! And the book collection was great. Highly recommend!

Cozy Family Retreat with Saco River Access
Our 3rd time staying here....great location and reasonably priced. Love the view out back to the trees and a peek of some mountains. Also great snow cleanup - we were here for a big storm and the plows cleared the car park and the paths were shoveled quickly.

2 bedroom condo, mountain views, pools and jacuzzi
Lorraine’s place was perfect for our stay. We would recommend it for anyone visiting the area.

Cozy Mountain Getaway For All Seasons
We had a great day! The place was perfect for our small group, and very convenient to the mountains for skiing. The condo had all the little things needed. And it was very comfortable. I would definitely book again.
Quick stats about vacation rentals with outdoor seating in Winthrop
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
1K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Sunday River Resort
- East End Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Popham Beach State Park
- Mt. Abram
- Samoset Resort
- Cliff House Beach
- Portland Museum of Art
- Sunday River Golf Club
- Wolfe's Neck Woods State Park
- Pemaquid Beach
- Pinnacle Park
- Coastal Maine Botanical Gardens
- West Shore Sandy Beach
- Pemaquid Point Lighthouse
- Big Beach
- Andrews Beach
- East End Beach
- Falmouth Country Club
- Portland Country Club
- Woodlands Country Club
- Bradbury Mountain State Park