Holiday rentals with outdoor seating in Middletown

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

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Popular amenities for Middletown outdoor seating rentals

Holiday House Rentals with Outdoor Seating

Guest favourite
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 favourite
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!
Top Guest favourite
Home in North Haven
5 out of 5 average rating, 144 reviews

Luxury Stay in Expansive Historical Home

Rebecca Rating, 5 stars1 week ago
The house was wonderful! We stayed for my daughter’s graduation and it couldn’t have been more perfect. The special touches like having the kitchen so well stocked and toiletries in all of the rooms was especially nice, and the house had plenty of room for everyone to relax and spread out. We thoroughly enjoyed our stay!
Guest favourite
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 favourite
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 favourite
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!
Top Guest favourite
Home in East Haddam
5 out of 5 average rating, 24 reviews

Pet-Friendly Getaway in Historic East Haddam Home

LaurenRating, 5 stars1 week ago
Me and a few friends spent the weekend at Lauren’s since we had a wedding in East Haddam. Lauren’s home was lovely, and we especially loved the friendly chickens in the backyard! The beds were extremely comfortable and the home was perfect for our needs. Thank you so much for having us!
Top Guest favourite
Home in Higganum
5 out of 5 average rating, 22 reviews

The Doll House

EthlynRating, 5 stars5 days ago
Jeremy’s “Doll House” was a charming little place on lovely peaceful grounds. The location was very convenient for visiting our Connecticut relatives and attending our granddaughter’s graduation. His kitchen is well stocked with all the essentials and then some. Everything was very clean and the bed was very comfortable. There is a huge walk in closet in the bedroom and great laundry area in the bathroom. I would recommend Jeremy’s place and would stay there again.

Apartment rentals with outdoor seating

Guest favourite
Apartment in East Lyme
4.96 out of 5 average rating, 120 reviews

Lakefront Luxury on Pattagansett

KaiRating, 5 stars3 weeks ago
Staying at Kevin’s place was such a reset from Manhattan. It was cozy, comfortable and very breathtaking. Kevin has great response time and is willing to assist you while you stay. Will definitely be back soon!
Top Guest favourite
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 favourite
Apartment in Middlebury
4.92 out of 5 average rating, 121 reviews

Cozy Apartment with Water View of Brook

EvelindaRating, 5 stars1 week 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!
Guest favourite
Apartment in Winsted
4.91 out of 5 average rating, 380 reviews

Gateway to the Berkshires

ThayerRating, 5 stars1 week ago
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.
Top Guest favourite
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 favourite
Apartment in Brookfield
4.92 out of 5 average rating, 281 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Jose CarlosRating, 5 stars2 weeks ago
The place was really nice and the host was great! Don’t get discouraged if the power goes out during your stay cause apparently that’ll happen 2-4 times a year according to the host. Other than that I highly recommend
Top Guest favourite
Apartment in Milford
4.98 out of 5 average rating, 104 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

JudyRating, 5 stars1 week ago
Dawn and Bob’s place is one of the top Airbnb’s we have stayed in! Top notch in every way. It was spotless, comfortable and had everything we needed. And on top of that Dawn and Bob were the most friendly hosts we have met! I would recommend this Airbnb without reservation and will be back whenever we are back in CT!
Top Guest favourite
Apartment in Simsbury
4.99 out of 5 average rating, 342 reviews

Ensign House Room

AllisonRating, 5 stars1 week 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 favourite
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 favourite
Condo in Uncasville
4.98 out of 5 average rating, 108 reviews

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

MelindaRating, 5 stars6 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 favourite
Condo in Uncasville
4.94 out of 5 average rating, 32 reviews

Cozy Vacation Villa 5 minutes from Mohegan

WilliamRating, 5 stars3 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
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 favourite
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!
Top Guest favourite
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.
Superhost
Condo in North Fork
4.9 out of 5 average rating, 125 reviews

Seaside Summer Escape –2BR Waterfront Condo w/Pool

DebbieRating, 5 stars1 month 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 favourite
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 holiday rentals with outdoor seating in Middletown

  • Total rentals

    30 properties

  • Nightly prices starting at

    $77 AUD 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

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