Vacation rentals with outdoor seating in Middletown

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Middletown outdoor seating rentals

House rentals with outdoor seating

Guest favorite
Large glass doors frame a serene view of the lake, with gentle waves reflecting the sky's colors. A coffee table with a decorative plant occupies the foreground, while outdoor seating is visible beyond the doorways, enhancing the connection between indoor and outdoor spaces.
Home in Lake Pocotopaug
4.87 out of 5 average rating, 101 reviews

Beautiful Lake House on Lake Pocotopaug

EdithRating, 5 stars2 weeks ago
Beautiful home with great communal space for our family gathering. This is just what we needed. Thank you!!
Guest favorite
A serene garden space features lush green foliage and vibrant pink flowers, with a rustic wooden chair positioned to overlook a gentle waterfall. The surrounding trees provide a natural canopy, creating a peaceful atmosphere for relaxation.
Home in Chester
4.98 out of 5 average rating, 210 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

SarahRating, 5 stars2 weeks ago
This is our second visit in the Recycle House. It’s such a lovely oasis. We love all the unique touches and creative uses of materials throughout the house. The location just steps from the charming town of Chester could not be better. The perfect CT weekend getaway!
Guest favorite
A newly renovated bathroom features a double vanity with a smooth countertop and dark fixtures. A large mirror reflects ample lighting, while decorative baskets provide storage beneath. Natural light filters in through a window, complementing the clean and simple design.
Home in Manchester
4.98 out of 5 average rating, 50 reviews

2-BR Simplistic Retreat Minutes from Downtown

KellyRating, 5 stars4 weeks ago
Host went out of their way to make our stay special. We were down there for UConn graduation it was close to the school but far enough away to not be in all the traffic of graduation. Would highly recommended to other UConn parents and anyone visiting the area for school tours etc
Guest favorite
A serene lakeside view captures a vibrant sunset reflected on the calm water. The sky is filled with shades of orange and purple, framed by distant hills. A stone wall borders the foreground, leading into a pebbled area near the water's edge.
Home in Lake Pocotopaug
4.88 out of 5 average rating, 26 reviews

Lakeside Paradise with Breathtaking Sunsets

MaileeRating, 5 stars2 weeks ago
Amazing house! We rented the lake house and guest house to spend time with family and friends during our son’s graduation at Wesleyan. I stayed in the guest house. It was so cozy with great modern amenities. It was the perfect place to relax and close to the school. Being close the lake was a definite plus. I highly recommend!!!
Guest favorite
Four orange lounge chairs with side tables are positioned on a wooden deck beside a sparkling blue swimming pool. Flower pots with blooming plants are placed around the chairs. Lush greenery is visible in the background beneath a clear blue sky.
Home in Middletown
4.95 out of 5 average rating, 41 reviews

Hot Tub and pool Home away from home

KristenRating, 5 stars5 months ago
Jan's house was a great stay with plenty of room for six adults. We loved the game room and outdoor hot tub. Instructions for the hot tub were clear and easy to follow. We'd definitely stay again!
Guest favorite
The cottage exterior is framed by lush greenery, featuring a welcoming entrance with a white door accented by a wreath. Blue hydrangeas bloom in pots beside the steps, leading to a stone pathway that invites guests to explore the property.
Home in Lake Pocotopaug
4.94 out of 5 average rating, 17 reviews

Lake House, Pet-Friendly

KivieRating, 5 stars2 weeks ago
My wife, friends, and I had an awesome time, and Thomas is very thoughtful. Second time renting from him, and last time I mentioned we made smores. For my wife, it was her first time. Guess what? He left us a smores kit! Thanks again, Thomas!
Guest favorite
A spacious living area features natural wood beams and light-colored furnishings. A large plant sits in a ceramic vase on a round table, while a comfortable sofa arrangement is placed around a central coffee table. Multiple windows provide ample natural light.
Home in Haddam
4.97 out of 5 average rating, 29 reviews

The Farmhouse Stay

MarisaRating, 5 stars2 weeks ago
Chelsea was communicative and helpful about her beautiful house. It had all we needed, was well appointed, beautifully decorated and in a gorgeous natural setting. We spent time lounging in the living room as a family and it was so comfortable. Top notch! Grab this place now!
Guest favorite
A modern kitchen features sleek black cabinetry and stainless steel appliances. A large island with bar seating is centered, adorned with a vase of fresh flowers. Natural light floods in through the windows, and a sliding glass door leads to the outdoor deck.
Home in Lyme
4.92 out of 5 average rating, 331 reviews

Stunning, peaceful and private home

KimRating, 5 stars1 month ago
The house was great and we were able to get Ubers to go to dinner. Beautiful house and stocked with everything you would need. We were on a girls weekend and had trouble with the locks but we just used the key. It could have just been us. We had a wonderful time and enjoyed the home.

Apartment rentals with outdoor seating

Top guest favorite
The exterior of the two-story home is showcased, featuring a light-colored facade with multiple gabled roofs. A well-maintained lawn surrounds the house, accented by blooming shrubs. A paved driveway leads to a two-car garage, and trees provide a natural backdrop.
Apartment in Waterbury
4.99 out of 5 average rating, 102 reviews

Everything you need! Apartment!

KiraRating, 5 stars2 weeks ago
Jerry is an amazing host and has a great place to stay. You will find everything you need for a short or long stay with the full kitchen. The AirBnb is in a quiet part of Waterbury, right on the edge, and has a grocery store less than 10 minutes away by car on a low traffic side road. Highway 84 is less than 10 minutes in the other direction and lets you go explore the rest of Connecticut and return back after a long day with ease. This is our second time staying at this AirBnb and it was just as wonderful as the first time. Can't recommend this place enough for anyone looking to stay in the area!
Top guest favorite
The exterior of the rental unit is framed by mature trees, with a front porch featuring a railing and rocking chairs. A stone wall lines the driveway, leading up to the entrance. Soft greenery surrounds the area, creating a serene environment.
Apartment in Chester
4.98 out of 5 average rating, 167 reviews

Charming Chester Retreat - Cottage

JackieRating, 5 stars1 week ago
Wow!!! This is the nicest airbnb I have ever stayed in. The property is beautiful and peaceful, surrounded by trees with lots of privacy. The cottage itself is immaculate (I’m very particular about cleanliness). The dining area is stunning with skylights and beautiful trees outside and great light! The hosts were also so welcoming and friendly, they included so many nice touches for my baby including a pack and play/travel crib, diaper changing area, and toys! I hope to stay here again every time we come to this area!
Guest favorite
A welcoming living space is shown, featuring a large flat-screen TV displaying a beach-themed greeting. A light wood dining table with chairs is set, accompanied by a fully equipped kitchen with wooden cabinets and modern appliances. Natural light filters in through the windows.
Apartment in West Haven
4.91 out of 5 average rating, 519 reviews

entire, private apartment close to the beach

KatieRating, 5 stars2 days ago
Alisa and Lena's place was really cute, private and comfortable. We had everything we needed for our 2 night stay. Also you can walk a few short blocks to a bird sanctuary!
Guest favorite
The living room showcases a comfortable seating area with a dark couch, complemented by a glass dining table nearby. A wooden mantel above a decorative fireplace adds warmth, while natural light filters through the large windows, illuminating the soft white walls.
Apartment in Ashford
4.97 out of 5 average rating, 254 reviews

Enjoy a Farm Stay without the Work

TheresaRating, 5 stars3 weeks ago
This was a delightful stay, and I wish we hadn't had so many family obligations so we could have enjoyed the place better. I so wanted to take time to relax on the beautiful and inviting back patio and just explore the property. I love historic places. We will definitely stay again next time we have family events in the area. Carol reached out to us and made us feel very welcome. We knew we had help if we needed something, but we didn't experience any issues at all, so didn't need to reach out. Great host for sure!!!
Guest favorite
A charming yellow cottage stands beside a flowing brook, with a paved walkway leading to a private entrance. Outdoor seating features a wooden table and chairs, while a lantern adds soft illumination. The surrounding trees are bare, indicating a cozy winter atmosphere.
Apartment in Middlebury
4.92 out of 5 average rating, 121 reviews

Cozy Apartment with Water View of Brook

EvelindaRating, 5 stars6 days ago
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!
Top guest favorite
A comfortable living area is presented with a gray sectional sofa and a wooden coffee table resting on a colorful area rug. Natural light enters through large windows, illuminating the hardwood floors and revealing a small antique chest and a decorative lamp.
Apartment in Deep River
4.93 out of 5 average rating, 147 reviews

Lovely Garden-Level Apartment in Heart of Town

ElizabethRating, 5 stars1 week ago
Lovely town and environment. Very spacious and fully equipped apartment. The two bedrooms are separated from each other by the big kitchen, a little reading room and the living room…so good privacy. Two TVs. Comfy beds! The small town is an easy and pleasant walk. It’s a ground floor apartment under the owners house, so be prepared for the patter of little dog feet above. We did not see the owners but communication was terrific. Great place to stay in the vicinity.
Guest favorite
Apartment in Brookfield
4.92 out of 5 average rating, 280 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

BridgetRating, 5 stars2 weeks ago
We had to cut our stay short due to changes in travel plans, which was a pity because it was a really lovely and very comfortable place. I would strongly recommend it and hope to stay longer next time.
Top guest favorite
A spacious sleeping area features a California king bed with light bedding. Decorative pillows add a soft touch. A stone wall and floral artwork enhance the room's character. Soft lighting from unique lamps provides a warm glow, complemented by a cozy seating bench at the foot of the bed.
Apartment in Simsbury
4.99 out of 5 average rating, 342 reviews

Ensign House Room

AllisonRating, 5 stars6 days ago
I had a wonderful three day stay at Courtney‘s historical Ensign- Bickford house apartment in the heart of downtown Simsbury. Walking distance to the flower Bridge, where I enjoyed coffee with the sunrise each morning of my stay! Apartment was lovely, clean, and Courtney was a very responsive host. Little details and amenities in the apartment, such as the delicious coffee, snacks, and seltzer water were a pleasant surprise! I am looking forward to staying again sometime soon in the future!

Condo rentals with outdoor seating

Top guest favorite
The main living area features a comfortable seating arrangement with patterned armchairs and a gray sectional sofa. A round coffee table sits in the center, complemented by dark poufs. Natural light enters through large windows, and a cozy fireplace adds warmth to the space.
Condo in Uncasville
4.97 out of 5 average rating, 36 reviews

Modern Loft Villa, 1 mile to Mohegan Sun

LauraRating, 5 stars3 weeks ago
just returned from annual moms weekend away...Erin's place was beautiful! well stocked, clean, looked just like the pics, great sound system. loved the extra little details like the large ice cubes already made (for me as an old fashioned snob), the adorable dry bar, and the decor in general w all the gold touches-it made it stand out from the typical! the best was walking in and smelling how fresh and clean and homey it was! would def recommend. also we had zero questions bc she was so proactive reaching out prior to checking in. check out her place! :)
Top guest favorite
The outdoor saltwater pool is framed by lush greenery and well-maintained landscaping. Sun loungers are positioned along the poolside, inviting relaxation. The backdrop features a charming gray multi-story building, visible behind white railings adorned with vibrant flowers.
Condo in Uncasville
4.98 out of 5 average rating, 108 reviews

CASiNO, Spa, Hot Tub, Pool, King bed, sauna

MelindaRating, 5 stars2 days ago
The Villa was exactly as described! Easy communication with owner. A perfect getaway weekend, every amenity we could want or need! Look forward to visiting again in the near future!
Guest favorite
A clean, rectangular outdoor pool is framed by a white fence and surrounded by colorful hanging flower baskets. Lounge chairs line the poolside, inviting relaxation under a wooden trellis that casts dappled shadows across the deck.
Condo in Uncasville
4.94 out of 5 average rating, 32 reviews

Cozy Vacation Villa 5 minutes from Mohegan

WilliamRating, 5 stars2 weeks ago
The stay was very peaceful, friendly neighbors. The scenery was great, Desiree was there for any concerns we had, and with timely response. I would anyone that want a pleasurable stay while in Norwich, this is the place to be. Thanks again, for a wonderful stay. William & Potreen
Superhost
A cozy living area is furnished with a beige sofa, a round wooden coffee table, and stylish light blue armchairs. A large window allows natural light to fill the space. Potted plants add a touch of greenery, creating a relaxed atmosphere.
Condo in Old Saybrook
4.89 out of 5 average rating, 73 reviews

Seashore getaway - CT shoreline

ScottRating, 5 stars2 weeks ago
Lauren was great and her home was exactly as promised! Great stay and will stay again!
Top guest favorite
A living area features a comfortable sofa and two armchairs, arranged around a rustic coffee table. A fireplace is set into a stone mantel, and a large television is mounted on the wall. Sliding doors lead to a private balcony, allowing natural light to fill the space.
Condo in Uncasville
4.98 out of 5 average rating, 137 reviews

The Vacay Villa

SusanRating, 5 stars3 weeks ago
This is a wonderful property that is close to everything we like to do! Krista is a wonderful host and I’m always excited if her place is available.
Top guest favorite
A spacious bed is adorned with a plush, white comforter and decorative pillows, including one reading 'home.' A tray with refreshments and a poolside bag rests nearby. Soft lighting from bedside lamps enhances the room's calm ambiance, complemented by a framed landscape photograph on the wall.
Condo in Uncasville
4.98 out of 5 average rating, 182 reviews

Peaceful Oasis steps from Mohegan Sun

EricRating, 5 stars2 weeks ago
We had a great time and the property was immaculate! The hosts came by with extra towels quickly upon request and it was a holiday. Recommended!
Superhost
A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.
Condo in North Fork
4.9 out of 5 average rating, 125 reviews

Seaside Summer Escape –2BR Waterfront Condo w/Pool

DebbieRating, 5 stars3 weeks ago
We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!
Guest favorite
Two blue Adirondack chairs are positioned on a manicured lawn, facing a vibrant sunset over the ocean. The sky displays pink and orange hues as the sun sets on the horizon, creating a serene outdoor setting.
Condo in North Fork
4.92 out of 5 average rating, 139 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

MorganRating, 5 stars2 weeks ago
We had a great stay! Instructions were clear and the home had everything we needed.

Quick stats about vacation rentals with outdoor seating in Middletown

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$10,490 GYD before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore