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Vacation rentals with outdoor seating in Middletown

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Middletown

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Rental unit in East Haddam

4.78 out of 5 average rating, 275 reviews

The Federal Suite at the Wisteria Rest

The apartment is beautiful and fully furnished in the historic District of East Haddam close to Rt 9 or 2, the Goodspeed Opera House, River House and CT Shoreline. Gillettes Castle, Fox Hopyard, Devils Hopyard, & more. Just 20 minutes to Middletown and wonderful dining. This apartment is in the 1800 section and has some quirky things to be aware of, floor that have uneven heights, stairs to the bedroom and , a claw foot tub/shower that you have to step into and a full flight of stairs to get in.

Guest suite in Lebanon

4.96 out of 5 average rating, 116 reviews

Relaxing, Rural one Bedroom with Private Kitchen and Bathroom at Mannamour Homestead

Relaxing country setting secluded off a long private driveway, on a dead end road, in historic Lebanon, Connecticut. Horses line the driveway, and chickens roam the yard. Sunrises over the backyard among the tree covered hills. The private accessory apartment, attached to the main home, includes one bedroom, living area, kitchen, bathroom, & porch. Witness the bustle of the active homestead. Relatively close to landmark Casinos (Foxwoods & Mohegan Sun), hiking, the shoreline & historic sites.

Guest suite in Bethlehem

4.99 out of 5 average rating, 257 reviews

Breezy Crest private & restful w/antique charm

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and ski slopes.

Guesthouse in Glastonbury

4.94 out of 5 average rating, 145 reviews

Unique luxurious private building in historic area

Unique private space for sophisticated adult(s). Located just 7 miles from downtown Hartford, 1 mile from Route 2 & 84/91 interchange. Guests may relax in this completely renovated historic Barn, with covered parking, away from street view. Enjoy this luxurious space and the private gym which includes treadmill, eliptical, bike, free weights, boxing bags, and yoga space. Upstairs, walk the catwalk between spacious bedroom and full sized Office / Loft over looking historic Main Street.

Home in East Haddam

4.94 out of 5 average rating, 158 reviews

Romantic Getaway at The Lake!

Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located, 30 minutes from Hartford, 30 minutes from the Mohegan Casino.

Condo in Norwich

4.95 out of 5 average rating, 130 reviews

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf

Spa Resort | Casinos | Heated Seasonal Pool and Hot Tub | Sauna | Fitness Room | Clubhouse | Golf | Restaurants | Heated Massage Chair | Warm Robes and Blankets | Electric Fireplace with Remote| New Serra topper Whether you’re looking to get away or jump in, enjoy this relaxing retreat surrounded by upscale amenities! We’ve done our very best to ensure your stay is comfortable and tranquil, full of necessities and extras, and that there are many nearby options for adventure and fun.

Guesthouse in Portland

4.99 out of 5 average rating, 149 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Home in Haddam

5 out of 5 average rating, 104 reviews

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

Home in Bristol

4.91 out of 5 average rating, 151 reviews

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Home in Lyme

4.97 out of 5 average rating, 235 reviews

“The Answer” Your Unique, Tidal, Riverfront Escape

“The Answer” is listed in “Only In Your State” 2024 - titled “This Riverfront Retreat Will Be Your New Favorite Destination” and Travellers Worldwide 2022 and 2023 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil tidal water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

Rental unit in New Britain

4.94 out of 5 average rating, 145 reviews

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

Guest suite in Wallingford

5 out of 5 average rating, 545 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station.

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Popular amenities for Middletown outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Home in East Haven

4.96 out of 5 average rating, 132 reviews

The Breakaway - a waterfront gem.

Home in Milford

4.98 out of 5 average rating, 192 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Home in Coventry

5 out of 5 average rating, 121 reviews

Waterfront 10 min to Uconn outdoor tv gas fire pit

Home in Vernon

4.99 out of 5 average rating, 136 reviews

Luxe Bolton Lake

Home in Plymouth

4.97 out of 5 average rating, 100 reviews

Charming 3BR Hill House *Remodeled* w/Arcade

Home in Bethlehem

4.97 out of 5 average rating, 286 reviews

Litchfield County Farmhouse with a Modern Twist

Home in Hamden

4.92 out of 5 average rating, 103 reviews

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

Home in Litchfield

4.93 out of 5 average rating, 177 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Apartment rentals with outdoor seating

Rental unit in Milford

4.94 out of 5 average rating, 137 reviews

The Boathouse, private downtown Harborside suite

Rental unit in Mansfield

4.98 out of 5 average rating, 281 reviews

Green Energy Ecohaven

Rental unit in Torrington

4.98 out of 5 average rating, 151 reviews

Apartment on Main St.

Rental unit in Chester

4.98 out of 5 average rating, 156 reviews

Charming Chester Retreat - Cottage

Rental unit in Winchester

4.91 out of 5 average rating, 369 reviews

Gateway to the Berkshires

Rental unit in Deep River

4.93 out of 5 average rating, 134 reviews

Lovely Garden-Level Apartment in Heart of Town

Rental unit in New Britain

4.78 out of 5 average rating, 196 reviews

Comfort & Warmth Included: Your Escape, Reimagined

Rental unit in Simsbury

4.99 out of 5 average rating, 304 reviews

Ensign House Room

Condo rentals with outdoor seating

Condo in Litchfield County

4.95 out of 5 average rating, 19 reviews

Pacer's Pasture

Condo in Norwich

5 out of 5 average rating, 18 reviews

Modern Loft Villa, 1 mile to Mohegan Sun

Condo in Norwich

5 out of 5 average rating, 73 reviews

KING bed! Hot tub! Pool! Spa! Casinos! Hot tub!

Condo in Fairfield

4.83 out of 5 average rating, 135 reviews

Cozy Condo by Fairfield U/SHU | Patio | Wshr/Dryr

Condo in Norwich

4.94 out of 5 average rating, 17 reviews

Cozy French style Villa-3 Bed-Casino-Pools-Jacuzzi

Condo in Norwich

4.93 out of 5 average rating, 28 reviews

Cozy Vacation Villa 5 minutes from Mohegan

Condo in Norwich

4.97 out of 5 average rating, 117 reviews

The Vacay Villa

Condo in Norwich

4.98 out of 5 average rating, 156 reviews

Peaceful Oasis steps from Mohegan Sun

Quick stats about vacation rentals with outdoor seating in Middletown

Total rentals
40 properties
Nightly prices starting at
$40 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