
Holiday rentals with outdoor seating in Litchfield County
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Litchfield County
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Holiday House Rentals with Outdoor Seating

Beautiful Lakefront Retreat with Private Dock
A gem of a home if you’re looking for a waterfront property with great lake access. David’s home is well stocked with everything you need - from baking to cooking , from laundry to great choices of board games , a nice library if reading by the water is what you care to do . If you’re a bass fisherman like me , you have direct access to Squantz Pond, which can be a great fishing alternative to nearby Candlewood Lake. The property is close to the main road and traffic can be a nuisance to folks who are not used to it . City folks like me don’t mind it. David was a great host , very responsive . There was a slight miscommunication during check in , but that was taken care of right away . My family hopes to come back again . BTW, for those who don’t know how to play the piano , take some brief lessons before coming and impress your folks. Joe

Stay at Old Dorset Farm & create lifelong memories
We had a wonderful stay. The home is beautiful, and the hosts were very thoughtful. The crib we requested for our 1-year-old was already set up when we arrived, complete with a soft blanket and pillow. There was plenty of firewood for cozy fires in both indoor fireplaces, and our kids loved making s’mores outside. Ninka was warm, responsive, and helpful throughout our stay.

Best River View, on Rail Trail in Collinsville!
We stayed here for our wedding weekend and could not have asked for a more perfect place. The house was absolutely beautiful —spacious, thoughtfully stocked, and had everything we needed and more. The views were stunning and made the entire experience feel so peaceful and special. Carol was incredibly responsive and helpful throughout the entire process. This is truly a one-of-a-kind stay. Highly, highly recommend!

Litchfield Modern Farmhouse
The house is exactly what we needed and very well located. Near restaurants, in a beautiful neighborhood and privacy. It was clean, with a big pool, a lot of space outside and with all amenities that was described. I liked so much because the house is very illuminated . I want to stay in it again .

Secluded modern forest cabin with private brook
The charming house is in the most beautiful settings - tall trees with a creek running through. So peaceful! Secluded, but a short drive to cute shops and restaurants.

Connecticut Chalet - Private Pond, Firepit, Views!
My family had a great stay at Amanda's place. It was the perfect vacation spot - we really enjoyed the panorama view! Everything was just as described and we felt right at home.

Rustic Swedish Barn/Featured in Airbnb Magazine
We enjoyed the perfect escape from the city in this magical barn with gorgeous antiques and pristine views. Definitely will be back for future celebrations!

Sunrise on the Water's Edge - Riverside Bungalow
What a great spot! Beautiful views on the river and a good spot for a family of 5 to use as home base while visiting Six Flags. Top notch host, thanks for everything Zuhair!
Apartment rentals with outdoor seating

West Main
Loved this little apartment. It has everything you need and more.

Private Berkshire Barn Apartment
Went for a Berkshire School reunion the two of us, perfect spot. Charming quiet grounds, perfect location for accessing Berkshire School, clean, Keurig, comfortable bed, amenities as stated (and quick confirmations from host), super easy process for check in and check out. Asked many questions and host responded very quickly and was very friendly in her communications.

*The Ridge House*
We had a great time at The Ridge House! The property was gorgeous, and the creek is even more stunning in person. The apartment was clean, fresh, and felt very cozy. The kitchen was well stocked to make a meal. Instructions were clear and we had no logistical issues. Thanks for great stay!

Charming apartment with breathtaking view!
Highly recommend Patrick and Monica’s location. You feel right at home when you walk! The pool and patio views are breathtaking. The beds are very comfortable. Patrick was super responsive to my messages regarding restaurants.

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!

Modern Copake Falls Getaway - 8 Mins to Catamount
The Airbnb is on a small hill looking out towards a small pond and an open field. The sunset in particular was very nice. The home is in a very private location. Inside, the space was well decorated - simple yet tasteful. The space itself is on the smaller end but the decor opens up the space. Michael answered all questions within 24-hours. Easy to communicate with. Overall a good stay

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!

Hideaway with Spectacular Berkshire Views
I’ve visited many, many AirBNB’s over the years and Elisabeth and Ricky’s was one of the best. The accommodation is beautiful, it’s a lovely little converted flat above the garage, settled into the woods and garden. We were greeted by their corgi and by Elisabeth who both made us feel at home. We were able to wander their gardens, drink gin and tonics in the sun and generally make ourselves at home. A lovely couple and a highly recommended Airbnb.
Condo 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!

Spacious Condo • Quick Drive to Everything
Pete was very great person as a host . She treated us very well and I feel we felt like home great place to stay definitely be back.

Cozy one bedroom apartment in Wooster street
Maricela was very responsive and flexible throughout our stay and booking arrangements. Thank you!!

Quiet refuge in Great Barrington
Elaine’s place was absolutely perfect for what we needed; which was a comfortable, clean, private space that was close to a show we were seeing at the Mahawaie Theater. Only about a 5 minute drive, which Elaine assured us it was. Space was very private, with own bath which is important to us. Very clean, bed nice and comfy. Had refrigerator, microwave, coffee pot, tea pot, as well as coffee and tea !! Plus creamer in fridge. Would def recommend.

Cozy and charming retreat in quiet area of Wlfd.
Cristina's home was great for our stay! She was extremely helpful even before we checked in, providing clear instructions on where to park and the location of the entrance. She even left out some toys for our son to play with during our time there. It's small space, but what we needed and exactly as described in the listing. We would absolutely stay here again, when we come back to the area!
Destinations to explore
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- Fairfield Beach
- Yale University
- Six Flags New England
- Walnut Public Beach
- TPC River Highlands
- Thunder Ridge Ski Area
- Woodmont Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Bushnell Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Calf Pasture Beach
- Kent Falls State Park
- Wildemere Beach
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Sherwood Island State Park
- Bayview Beach
- Hudson Highlands State Park
- Brownstone Adventure Sports Park
- Anchor Beach
- South Pine Creek Beach