
Vacation rentals with outdoor seating in Middletown
Find and book unique accommodations with outdoor seating on Airbnb
Top-rated accommodations with outdoor seating in Middletown
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Middletown outdoor seating rentals
House rentals with outdoor seating

Bailey House
It was a lovely stay. Great location. House felt like a home and had great vibes.

Charming home ready for fun and/or relaxation!
We came to Norfolk for a show at the Infinity Music Hall. This house was a perfect landing spot to cook dinner before and relax after the show. It was so peaceful watching the snow fall from inside and the kitchen was perfectly stocked with everything we needed to cook. The appliances were top notch, the house was well decorated and we will definitely rent here again!

Welcome To Piper's Rest
It was wonderful stay and I’d go back anytime

Stylish Beach Getaway: pool & walking location
Maher’s house was an amazing peaceful experience. I enjoyed my time there and he had great recommendations to restaurants and activities! He was very responsive with all questions we had. I will totally stay here in the future if I can get the chance again!! Thank you Maher!!

Year Round Beach House in Old Saybrook, CT.- Pets
Laurie s place is very nice, spacious and clean. Plenty of space to eat, hang out and 2 bath. The fenced in yard is great for dogs or kids. We weren't in full summer season so we're not taking advantage of the beach and water options but they offer alot. Allowed for an early check in which was great as we were in town for a memorial service.

Maritime Village Getaway with Backyard
Mary’s Greenport home was a wonderful oasis during Spring Break! We loved waking up to rabbits hopping around the backyard in the morning. We enjoyed firing up the grill and sharing a meal outside. This is definitely great place to book if you have kids who love being outdoors (the yard is completely fenced in!) we loved being in close proximity to great shopping, beaches/parks & restaurants. We would love to visit again in the summer. Thanks for everything!

Long Island home w/ large pool
My stay here was phenomenal! From the host’s response time, down to the amenities that were placed throughout the house. As soon as you walk in, it felt like home. The house is spacious and highly functional. The design of the house offers a perfect blend of modern mixed with nostalgic elements. The best stay by far. Would love to book again!

Bright and Breezy Cottage by the Sea
My family and I have stayed at a ton of different airbnbs, vrbos and vacation rentals both stateside and abroad and I have to say Anne’s property is among one of the best we’ve stayed in. We were traveling with twin toddlers and the space was perfect. Anne is very friendly, the place is larger than we expected, very clean and you can tell Anne cares to the make the best experience possible. All the little touches were so wonderful - she has beach chairs, reusable beach bags, sunscreen, books, kids toys, coloring accessories, balls and toys, an outdoor game, hammock, lanterns, lights, fire pit and wood, you name it - it’s there. It was one of the most convenient stays we’ve had. We’d love to return and I couldn’t recommend it enough!!
Apartment rentals with outdoor seating

Modern Industrial Apartment with rooftop access
This Airbnb is so homey. We enjoyed our stay and will rent it again.

The Mystic Surfside Getaway 1-BD Apt
Our stay at Jennifer's place was excellent. We wish we could have stayed much longer. The apartment is in a quiet neighborhood just a few minutes drive from all the Mystic attractions (and a short walk from the very necessary wine shop and pizza joint! ) We loved our little balcony just outside the living room. My wife and I would absolutely stay here again!

Lakefront Luxury on Pattagansett
Kevin is a great Host - very responsible and accountable. We fully enjoyed staying his place. He was always willing to help while needed. The AirBnB is clean and has full of required amenities. We left some stuffs while checking out, he communicated quickly and shipped it out very fast. I highly recommend to stay at his place at East Lyme, CT.

Apartment on Main St.
As usual, I so much enjoyed my stay. Molly was hard at work in her beautiful flower garden, which are lovely to see first thing in the morning. I'll be back, for sure.

Charming apartment with breathtaking view!
Stayed here for 2 nights with a couple friends. Perfect spot for a quick getaway. Backyard and pool area was exactly what we were looking for with lots of space to lounge and relax. Lots of entertainment if you wanted to just hang inside as well. As some of the other reviewers noted, you can definitely hear the hosts move around upstairs. Didn't impact us too much except for Saturday morning. Was a little difficult to sleep in b/c of the noise.

Upscale Newly Constructed Apartment
The apartment was super clean and spacious! Has everything you need. Walkable to town and in a quiet neighborhood. Would definitely recommend Amanda’s place and would 100% stay here again!!

Squire Chase House
Great spot! Very walkable. It's also a great layout if traveling with small children - there is a separate meditation room upstairs that was perfect for setting up our travel cribs. Would stay again!

Cozy Apartment with Water View of Brook
Our stay was extremely quiet until the upstairs neighbors returned. We don't have kids or pets so we're very used to quiet. Getting used to hearing upstairs neighbors took getting used to for me. The place was chock full of supplies, coffee, Scrabble and welcoming decor. The bed was outstandingly comfortable. The bathroom was modern and creative! The outdoor patio, activities and view of the creek were impressive. This is definitely on our "to return to" list.
Condo rentals with outdoor seating

CASiNO, Spa, Hot Tub, Pool, Private Villa, Kingbed
Kim’s place was perfect for what me and my daughter needed. We were in the area celebrating her 15th birthday. The villa was clean, and quaint. The decor of the room was peaceful and warm. And most importantly it was CLEAN, no complaints! Kim was responsive and proactive in her communication. Will definitely visit again in the future and recommend to any friends and family who might travel that direction.

Seaside Summer Escape: 2BR Waterfront Condo w/Pool
Just as described, beautiful waterfront location that’s a 5 minute drive to town and local vineyards. Perfect weekend getaway

Montauk Waterfront Condo w/ Sunset Views
Absolutely wonderful stay and host. I've stayed at dozens of Airbnbs and this is one of my favorites! Doug's place is even better in person than the photos. We were a little nervous taking our first trip away with our baby, but it was extremely clean and comfortable, and Doug was so kind and responsive. The condo complex has a lovely boardwalk for taking walks, and the deck furniture was so comfortable to lounge in and take in the beautiful view. We hope to be back!

Peaceful Oasis steps from Mohegan Sun
We really enjoyed our stay. The villa was well decorated, clean, and cozy. It had such a relaxing vibe, I wish we had more time there. It was close to the casino and walking distance to the spa. It was great qetaway. The host also went out of the way to add personal touches.

The Vacay Villa
Krista place is very clean and welcoming. It had perfect personal touches. From coffee creamer for our morning coffee, to shower essentials. I find the small personal touches so nice and it is welcoming. Christa offered east check in and extended my check out time with no questions ask. This was a very nice place for a weekend trip and we will def be booking again!

Beachside Waterview 2Br Condo w/ Pool in Greenport
The place was perfect nice and clean what I like the best is the it was close to the beach to go for a walk.

Deluxe Studio Apt@The Montauk Manor
Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!

Coastline View Studio
This was absolutely perfect for our wedding weekend in Montauk. We were so close to everything which made it very convenient. The room was perfect and loved the clothing rack perk! Everything was clean and loved the skylights in the unit and the patio overlooking the water. 10/10 woud definitely stay here again!
Quick stats about vacation rentals with outdoor seating in Middletown
Total rentals
30 properties
Nightly prices starting at
$69 CAD 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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- Beach
- Fairfield Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Six Flags New England
- Quotonset Beach
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Giants Neck Beach
- Seaside Beach
- TPC River Highlands
- Clinton Town Beach
- Jennings Beach
- Amagansett Beach
- Shennecossett Beach
- Anchor Beach
- Attawan Beach
- Bushnell Park
- Thunder Ridge Ski Area
- Bayview Beach
- Long Island Aquarium