Vacation rentals with outdoor seating in Deep River

Find and book unique accommodations with outdoor seating on Airbnb

Top-rated accommodations with outdoor seating in Deep River

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

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Superhost

Guesthouse in Portland

4.98 out of 5 average rating, 242 reviews

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Superhost

Cottage in Old Lyme

4.82 out of 5 average rating, 164 reviews

New! “LaBoDee”

“LaBoDee”, a fun play on the word abode, house, is a tiny cottage located central to CT’s unique shoreline communities, just off I95. “LaBoDee” is one room with a fully equipped kitchenette, ready for those who would like to stay awhile. “LaBoDee” is on a property contiguous to a state forest (a trail is right outside the door) yet within walking distance is a delicious deli, market, gas station, pizza, a lake, and close by is the beach. A local restaurant has day passes for their beach- $20!!

Superhost

Home in East Haddam

4.93 out of 5 average rating, 241 reviews

Romantic Getaway at The Lake!

Beautiful year round getaway! 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 the Mohegan Casino.

Superhost

Loft in Essex

4.94 out of 5 average rating, 450 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. One bedroom on the ground floor with full bath nearby. The other bedroom is in the loft with queen bed with a daybed in the sitting area for two extra guests. We gladly welcome clean, well behaved pets. ($50 pet fee) Pet sitting and dog walking available for an additional fee. On site babysitting also available.

Superhost

Cottage in Westbrook

4.88 out of 5 average rating, 168 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.

Superhost

Home in Chester

4.86 out of 5 average rating, 103 reviews

Chester Cottage Waterfall House

A Bright Dreamy Colorful Warm Little House. The kind of spot to look at the stars at night and enjoy the sound of running water. Surrounded by Waterfalls, Rivers & Forests, close to Ferryboats, Steam Trains, Castles & Beaches. Five min stroll to Romantic Chester Village, Shops, Art Galleries, 9 Restaurants, and Microbrewery. . I am an artist and have my studio in the barn! (take a peek to see the latest sculptures ) Use our Glass House by the river for Yoga, Meditation, Dining, Hammocks

Superhost

Apartment in Chester

4.99 out of 5 average rating, 102 reviews

The Millhouse Downtown Chester

An upscale destination with accommodations for foodies & friends in the heart of historic Chester CT. Stay at this beautifully renovated historic Millhouse in charming downtown Chester. Enjoy strolling the streets loaded with shops, award winning restaurants, a microbrewery, art galleries, and more. All within a 1 minute walk. Our prime location is just 20 minutes to the CT shoreline and located in the heart of the CT River Valley. The Millhouse is next door to the Chester Historical Museum.

Superhost

Apartment in Chester

4.98 out of 5 average rating, 179 reviews

Charming Chester Retreat - Cottage

Book your Autumn Oasis now ❤️ This 2 bed, 1 bath unit has been redesigned to feature a modern kitchen, soaking tub and wood-burning fireplace. The unit also features a roof deck that overlooks our mature maple trees and a sprawling front porch, complete with rockers. Beach Access 10 min away at Cedar Lake. Great for 1-2 couples, small families or group of friends—Ask about our single roll away bed or pack' n' play(s). Kid friendly! New England getaway / Hidden Gem / Retreat/ Beach Access

Superhost

Cottage in Chester

4.97 out of 5 average rating, 287 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.

Superhost

Apartment in Deep River

4.94 out of 5 average rating, 156 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.

Superhost

Loft in Chester

4.99 out of 5 average rating, 154 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.

Superhost

Barn in Essex Village

4.96 out of 5 average rating, 164 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.