
Holiday rentals with outdoor seating in Sherman
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Sherman
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.
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Popular amenities for outdoor seating rentals in Sherman
House rentals with outdoor seating

Tranquil Tree-House on the beautiful Hudson River
A truly magical escape. This sacred treehouse was absolutely perfect - peaceful, stunning, and deeply rejuvenating. Rob and Roberta were the kindest, most thoughtful hosts I’ve ever encountered on Airbnb. Their warmth made the experience even more special. From sunbathing on the rocks and meditating in the grass, to yoga overlooking the water and cooking local organic meals - every moment was magic. Already planning my return. Thank you, Roberta and Rob!!

The Farmhouse
This was a gorgeous place with beautiful furnishings, warmth and charm! We will travel out of our way for a revisit. Very highly recommended!

Private Hudson Valley Country Retreat
My friends and I stayed in Stormville for a girls trip. The house is even better than the photos. The property and landscaping are stunning, we loved just staring out at the view with a cup of tea. The kitchen was impressively stocked with lovely teas and all the cooking gear we needed. Check in and communication were effortless. The location while a bit far from groceries (15m drive) was no more than 15-30m from lots of activities, small towns and hiking trails. We also loved how accessible it was from Metro North as we were coming from the city for just a short trip. It was very easy to get to and we all couldn't stop talking about how we hoped to return. Highly recommend!
Woodstock Historic Artist Estate - The Pond House
No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.

Cheerful 2-bedroom house porch and fireplace
We had a great time relaxing in this cozy house and we love the screened porch. It's a wonderful house in a great location -close to everything.

Eagle Rock House
Edina and Glen's house was beautiful, spacious, and pristine. It was the perfect setting for a "girls weekend". The grounds were stunning, and made for a great setting. Very close to town, shopping, and wonderful restaurants. We really appreciated that our hosts were very proactive in reaching out and making all instructions clear. They were communicative and flexible. Thank you for having us in your beautiful home! Very memorable weekend.

Litchfield County Farmhouse with a Modern Twist
Wow! This home was such a “wow”—just perfection. The location is spectacular (peaceful and beautiful) and the home was everything you could ask for (a work of art, comfortable, functional, family friendly). We were in town for our son’s graduation from The Woodhall School and Scott’s home was the cherry on top of a perfect weekend. Highly recommend!

Idyllic retreat on the water <1.5 hrs to NYC.
My family and I absolutely loved Jonathan's place and would highly recommend the stay. The place was beautiful inside and out, the pictures dont even do it justice! Jonathan was a wonderful host, responsive and friendly. One of my favorite airbnbs, amazing setting dont miss this one!
Apartment rentals with outdoor seating

Apartment on Main St.
Gracious host, friendly and responded very quickly. The Airbnb itself was pleasant, quite cozy with a pretty backyard/garden area. Would definitely recommend to someone looking to stay in the area

Cozy Apartment with Sauna in Historic Stone Ridge
Very convenient location close by to everything we needed! We did have an issue with something in our unit, but Aaron communicated very quickly and was able to let us use the other available unit for the night. Both Air bnbs at the property were very well stocked and spotless. Felt very much at home here!

Spacious Cozy Guest Suite
We booked this place to be close the the festival downtown and it was. 1.3 miles or 25 minutes walk. Perfect for us. The Airbnb was clean and spacious. Shower is a little small but ok. King bed is very comfortable. Yummy welcome treats on the table was a nice touch. Keurig pods and maker available for your pleasure. Well lit and very secure. Felt safe at all times. Great place to book if you need to stay in this area.

Gateway to the Berkshires
The place was beautifully decorated and everything from the plants to the antiques was wonderful to see. This is the perfect place for any stay and they only ask that you respect the possessions. John was very responsive in helping us for a late check in.

King 1BR Apt with Cozy Den and Luxury Amenities
Very clean and comfortable! Tatenda is so sweet and responsive. Walkable to Yale and great restaurants, but also includes covered, safe parking in the building. We had fun grilling a dinner by the outdoor pool. Well-equipped workout rooms and the coffeemaker in the lobby was amazing offering a variety of options. We enjoyed everything about this Airbnb and will likely be back! Thank you Tatenda and Hyatus!

Private space, with yard
We had a great stay here as we explored nearby things (the Chuang Yen Monastery was delightful!) and visited some favorite spots. The weather was a little dreary when we were there, otherwise we would have made good use of the beautiful outdoor space. It was the perfect place for us to relax after our adventures every day—very quiet, very comfortable, clearly-written instructions for everything. We would be very happy to return!

Cozy Apartment with Water View of Brook
We were recently in town to visit family, staying at Traci’s made our visit enjoyable and relaxing. Check-in was easy, the apartment was clean with a comfortable bed and a peaceful view of the brook. Overall, we had a pleasant stay, thank you Traci!

Woodland Neighborhood Retreat
Worth every penny. Lisa was super responsive, the space was so welcoming and the surroundings were gorgeous. It was exactly what I was looking for in a little home away from home getaway.
Apartment rentals with outdoor seating

Pacer's Pasture
Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!

Trailside At Hunter-Phase II-Hunter NY
This condo is absolutely beautiful and comfy! We especially love the bed and pillows.

Scenic Getaway with Private Deck
Daria and Justin were lovely, responsive hosts. It’s a great little apartment — super clean, well equipped with all the basic necessities, tasteful, well thought out decor, a really pleasant place to be, right on the mountain. Small, but perfect for a couple or small family ski weekend. I would definitely recommend and would love to go back.

Bright & Cozy | Walk to Rail Trail
Well designed, well maintained modern style home. Love the warm toned interior. Quick drive to lots of hiking spots which was what brought us here. Management team was very professional and easy to communicate. Will consider for any future trips to Minnewaska/Mohonk.

Cozy West Point Hide Away and Cadet’s Get Away
Great Airbnb! Great Host! Perfect for visiting West Point

Stylish Condo Hunter Mountain
Host was responsive, place was tidy and instructions to get in and out are very clear. Place had an adequate lot as well and is also very peaceful

Trailside Tranquility at Hunter Mountain
Perfectly set up and spotless. The unit is supplied with everything you could possibly need. By far the best organized, supplied and clean Airbnb we have ever stayed in.

Hunter Mountain 2BR Condo - Steps to Slopes!
This is my second stay at Daniel’s, and it was just as good as the first! I love the location of his place in relation to the mountain. It’s a quick walk up the parking lot to the trails/lifts. Most importantly, my pups feel right at home, and they know his place now! His home is always clean and the linens/towels always smell fresh! I told him I will be coming back multiple times throughout the snow season to go boarding. He is very responsive and helpful and would go out of his way if need be! Overall, 12/10 recommend Daniel’s spot!
Quick stats about holiday rentals with outdoor seating in Sherman
Total rentals
30 properties
Nightly prices starting at
₹6,031 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Fairfield Beach
- Yale University
- Rye Beach
- Rye Playland Beach
- Minnewaska State Park Preserve
- Walnut Public Beach
- TPC River Highlands
- Thunder Ridge Ski Area
- Woodmont Beach
- Ringwood State Park
- Rye Town Beach
- Seaside Beach
- Bushnell Park
- Calf Pasture Beach
- Jennings Beach
- Silver Sands Beach
- Bash Bish Falls State Park
- Sunken Meadow State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Centerport Beach
- Walkway Over the Hudson State Historic Park
- Sherwood Island State Park
- Rockland Lake State Park