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Vacation rentals with outdoor seating in Middlesex County

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Middlesex County

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.

Rental unit in Chester

4.93 out of 5 average rating, 348 reviews

Chester Village 'Pied-à-terre' above art gallery

ONE night stays are available for last minute bookings, message us! If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled livingroom w/high ceilings, quiet, private bedroom in back, and w/large private deck overlooking Pattaconk Brook. A true gem, set up solely for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique, and neighbor to some of the BEST restaurants, art and shopping in CT!!!

Cottage in Westbrook

4.88 out of 5 average rating, 128 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Home in East Haddam

4.94 out of 5 average rating, 159 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.

Cottage in Chester

4.98 out of 5 average rating, 253 reviews

Updated cottage "Beriozka" on Cedar Lake

Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

Guesthouse in Portland

4.99 out of 5 average rating, 152 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!

Rental unit in Deep River

4.93 out of 5 average rating, 134 reviews

Lovely Garden-Level Apartment in Heart of Town

This garden-level apartment is centrally located within walking distance to Main Street's retail shops, restaurants, and grocery/pharmacy, and just minutes from The Lace Factory and Deep River Landing, Essex Steam Train & Riverboat, Connecticut River Museum, the CT shoreline and beaches, and so much more. A charming historic home over 200 years old with a classic New England feel, the apartment has two bedrooms, one full bath, and an eat-in kitchen complete with amenities.

Loft in Chester

4.99 out of 5 average rating, 115 reviews

The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK

Located in charming downtown Chester, our loft rests above the newly established Village Bistro; with the loft being situated above our restaurant and on Main Street please keep in mind that you may hear some background noise during normal business hours. Additionally, you will be staying in a 200-year-old structure so there is some quirkiness that goes along with an aged building such as ours but rest assured you will feel right at home in this cozy, warm, historic space.

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.

Barn in Essex

4.97 out of 5 average rating, 143 reviews

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Loft in Essex

4.94 out of 5 average rating, 429 reviews

Unique apartment in former art gallery.

The apartment is private and in a separate wing of a converted factory complex which includes an owner occupied building and artist studio in a quiet residential neighborhood. We gladly welcome clean, well behaved pets for an extra fee of $50. Pet sitting and dog walking also available for an additional fee. On site babysitting also available for an additional fee.

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Cottages

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Apartments

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Popular amenities for Middlesex County outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Home in Old Saybrook

5 out of 5 average rating, 25 reviews

Romantic Couples Retreat with Private Sandy Beach

Home in Clinton

4.96 out of 5 average rating, 114 reviews

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

Home in East Hampton

4.98 out of 5 average rating, 60 reviews

Lake Fun: PingPong, Pool Table, Slide, EV Charger

Home in Essex

4.98 out of 5 average rating, 51 reviews

Ideal Historic Home in Essex Village

Home in Essex

4.96 out of 5 average rating, 68 reviews

4-Bedroom Farmhouse *Comfort and Privacy*

Home in Madison

5 out of 5 average rating, 42 reviews

Writer's Retreat & Explorer's Adventure!

Home in Haddam

4.96 out of 5 average rating, 25 reviews

The Farmhouse Stay

Home in Clinton

4.79 out of 5 average rating, 42 reviews

LONG-TERM Glass House-Fall/Beach 5mins/Ski 25mins

Apartment rentals with outdoor seating

Rental unit in Clinton

4.97 out of 5 average rating, 36 reviews

Shoreline Oasis

Rental unit in Branford

4.94 out of 5 average rating, 18 reviews

Stony Crk Studio ideal for trvl nurses…

Rental unit in Killingworth

4.88 out of 5 average rating, 33 reviews

Life on the Farm

Rental unit in Westbrook

5 out of 5 average rating, 5 reviews

Private Guest Suite Water Views

Rental unit in Guilford

4.97 out of 5 average rating, 60 reviews

Cozy Private Lake Q Retreat

Rental unit in Chester

4.99 out of 5 average rating, 88 reviews

The Millhouse Downtown Chester

Rental unit in Clinton

4.98 out of 5 average rating, 66 reviews

Cozy Shoreline Getaway

Rental unit in Branford

4.97 out of 5 average rating, 103 reviews

Ridgeview Suite at Stony Creek Depot

Condo rentals with outdoor seating

Condo in Norwich

5 out of 5 average rating, 73 reviews

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

Condo in Greenport

4.83 out of 5 average rating, 124 reviews

Seaside Escape w Pool, Private Beach + Patio

Condo in Greenport

4.88 out of 5 average rating, 147 reviews

Beautiful Waterview Condo on the North Fork of LI

Condo in Norwich

4.98 out of 5 average rating, 156 reviews

Peaceful Oasis steps from Mohegan Sun

Condo in Norwich

4.97 out of 5 average rating, 117 reviews

The Vacay Villa

Condo in Greenport

5 out of 5 average rating, 107 reviews

"Breathtaking Waterfront Water's Edge view"

Condo in Greenport

4.92 out of 5 average rating, 137 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Condo in Groton

4.97 out of 5 average rating, 70 reviews

Steps from Downtown Mystic / Newly Renovated

Destinations to explore