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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Guest favorite

Guesthouse in Essex

4.82 out of 5 average rating, 28 reviews

Privateers Boathouse (Village Waterfront)

Right in the middle of all Essex Village offers: shopping, dining, boating. Short drive to beaches, farmstands, golf, hikes, theatre, colleges & more. Very special little waterfront cottage with unrivaled views, private deck & access to town. Park your car once and enjoy all the wonders of Essex Village by foot during your visit. 🌟 Secluded, yet utterly central Village location. 🛶 Access to swimming pool WITH ARRANGEMENT (2 towels provided) 🚣‍♀️ No proper launch for kayak/SUP- but several close

Guest favorite

The sunroom features a light pink wall and a high ceiling with exposed beams. A comfortable wicker sofa with decorative throw pillows accompanies two matching chairs. A patterned area rug covers the floor, while a small table sits in the center. Soft light filters through sheer curtains.

Cottage in Guilford

4.93 out of 5 average rating, 267 reviews

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

Top guest favorite

The expansive patio area features a large pool with a unique shape, surrounded by sun loungers and shaded seating options. A hot tub is positioned nearby, and additional amenities include a fire pit and a shaded cabana. The enclosed space is accentuated by landscaped elements.

Home in East Haddam

4.98 out of 5 average rating, 51 reviews

Spacious 5 bdrm, 6 bth, 30 min to beach & casinos

Spacious 5 bedroom 6 bath sleeps 14 -WHAT YOU’LL LOVE- • Private resort style patio, including STUNNING POOL, HOT TUB, fireplace and firepit, bar and grill, 65" TV, outdoor bathroom and shower. • Open concept floor plan that is great for groups and families. • Authentic New England experience. • Fun game room for adults and kids with wet bar and mini fridge • Quiet street and neighborhood. NY times listed East Haddam in their “52 places to love” in 2021 1 mile to East Haddam Center

Guest favorite

A spacious outdoor seating arrangement features comfortable wicker couches with plush cushions, positioned to offer unobstructed views of the tranquil water and surrounding landscape. The backdrop showcases a serene waterfront bordered by lush greenery and a clear blue sky.

Home in Guilford

5 out of 5 average rating, 10 reviews

3BR Waterfront Oasis on Joshua Cove, Private Beach

Kick back and relax in this modern, stylish waterfront home with a private beach. Newly renovated, this house offers beautiful, unobstructed views of the Long Island Sound and a backyard equipped with an outdoor patio & dining area, hammock, firepit, adirondack chairs, chaise lounges, and cushioned outdoor furniture (in season). You can enjoy swimming at the home's private beach in summer, leaf-peeping in fall, and bird watching in spring. The house is located 5 minutes from downtown Guilford.

Top guest favorite

A charming red cottage is framed by a white picket fence, surrounded by a well-maintained lawn dotted with shrubs and small trees. Large windows offer a glimpse of the inviting interior, while a curved entryway draws attention to the welcoming facade.

Guesthouse in Old Lyme

4.98 out of 5 average rating, 53 reviews

Studio Four-Entire Guesthouse near CT River

Take it easy at this unique and tranquil getaway. Studio Four offers an architecturally dynamic space flooded with light nestled into the landscape to embrace the pastoral surroundings. Close to the Connecticut River the property is private and offers its guests access to a private dock association on the Connecticut River at Goose Island, Lords Cove. You have access to a kayak launch and bikes, and can hike the neighborhood nature preserve which takes you to a scenic vista on the CT river.

Guest favorite

An open living area features a light-colored wooden floor, with a cozy gray sofa adorned with dark blue cushions. A round, wooden coffee table is positioned in front. A mirror and framed art decorate the walls, while a ceiling fan offers a gentle breeze.

Home in Old Saybrook

4.94 out of 5 average rating, 16 reviews

Seas the Day at the CT Shoreline

Welcome to a slice of heaven by the water. Spacious 4BR updated beach cottage. Well-equipped kitchen, outdoor shower & gas grill. Sunny enclosed porches downstairs & upstairs. 2 decks for friends & family to stretch out while dining al fresco or simply lounging. 5 minute walk to 2 private beaches & 3 miles to 2 town beaches & the center for unique shops & eateries. Plus... fiber optic wifi, free coffee bar, games, bikes, beach toys, beach wagon & umbrellas. Spas, outlets & casinos nearby.

Guest favorite

A sunny pathway leads alongside a vibrant yellow wall of the house, bordered by stone. White outdoor chairs and tables are positioned neatly on a patio overlooking a serene river, with trees gently framing the scene in the background.

Home in Clinton

4.93 out of 5 average rating, 135 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Comfy cozy with amazing views of River. Convenient to beaches, and includes free pass to the Clinton Town Beach! The well-equipped, intimate kitchen overlooking the river is a pleasure for any cook. You will love our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to groceries, coffee shops and amazing CT scenery! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants with music, and lots more.

Top guest favorite

Home in Westbrook

5 out of 5 average rating, 23 reviews

Secret Seaside Stone Cottage

Create unforgettable memories at the Secret Stone Cottage, your ideal retreat for family reunions or shared vacations in this scenic coastal New England town of Westbrook, Ct . Enjoy 2200 sq. ft. of living space nestled on the Patchogue River, with private dock access to Long Island Sound. Picture evenings spent grilling by the fireplace on the expansive patio, relaxing in the hot tub, or exploring the water by kayak and paddleboard....or a quick bike ride to beaches and restaurants.

Top guest favorite

A beautiful coastal sunset is displayed over a marshy landscape, with tall grasses swaying gently in the foreground. The sky transitions to warm hues of orange and pink, reflecting on the calm water, while distant houses are faintly visible against the horizon.

Home in Old Saybrook

5 out of 5 average rating, 49 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

Explore our Old Saybrook retreat on Great Hammock Rd, a cozy spot near the beach. Perfect for romance or family fun, it boasts stunning views and amenities. Relax in the hot tub, use bikes for local exploration, and enjoy evenings by the fire pit. Indoors, a fireplace adds warmth. Book now for a delightful getaway with views, memories, and the charm of Old Saybrook! Please note Our property is strictly an animal-free zone due to severe allergies persisting in the family.

Guest favorite

A charming cottage exterior is framed by wooden shingles and large windows, allowing natural light to fill the interior. A set of steps leads to the welcoming entrance. Outdoor seating is visible, accompanied by stacked firewood, creating an inviting outdoor space.

Cottage in Guilford

4.95 out of 5 average rating, 80 reviews

Direct Shoreline Long Island Sound Waterfront

A quintessential New England cottage with views of the water from all rooms. Spectacular sunrises and sunsets, enchanting panorama views. A stone's throw from the beautiful Grass Island state park and boat launch, a waterfront natural preserve, perfect for hiking or communing with nature. The interior underwent a full renovation in 2020 with new appliances and bath fixtures. Original structure preserved. A tranquil, quiet place.

Guest favorite

A charming home showcases a private deck adorned with planters and ample seating under a striped umbrella. Lush greenery surrounds the area, complementing the shingle-style exterior, and large windows invite natural light into the space.

Home in Westbrook

4.93 out of 5 average rating, 42 reviews

Private vacation home, close to beach

Welcome the our new Airbnb where serenity & style come together. Enjoy this charming, cozy home. Upon entering, you'll feel immediately relaxed & on vacation. This home is filled with natural sunlight light, large kitchen, stocked with with gourmet cookware & utensils. Outside you'll hear the babbling brook river, private large yard that offers outside patio deck for dining, entertaining or cuddling up by the fire pit.

Guest favorite

A cozy living area is featured with a comfortable sofa adorned with colorful cushions. Light floods in through a large window, highlighting the warm wooden floors and exposed beams. A small coffee table sits in the center, while a vintage cabinet and bar stools complete the inviting space.

Guesthouse in Madison

4.97 out of 5 average rating, 100 reviews

Chic Coastal Escape - 5 Mins to the Beach

Charming, spacious, and just 5 minutes to the beach, this one-of-a-kind carriage house is the perfect escape. Set on nearly an acre, it’s ideal for a romantic weekend, girls’ trip, or family getaway. Enjoy a private deck, huge backyard, and easy access to town, wineries, antique shops, seafood spots, and scenic trails. Relax, explore, and make unforgettable memories by the sea.