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House vacation rentals in Middlesex County

Find and book unique houses on Airbnb

Top-rated house rentals in Middlesex County

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

Home in East Hampton

4.95 out of 5 average rating, 230 reviews

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

Top guest favorite

A charming historic boathouse features a steeply pitched roof with shingle siding and decorative trim. A white picket fence surrounds the property, while blooming shrubs enhance the entrance. A balcony adorned with planters awaits above the front door, complementing the inviting facade.

Home in Greenport

4.98 out of 5 average rating, 101 reviews

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's, and recently & lovingly fully renovated and restored. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

A waterfront home with a unique tower design is reflected in the calm waters of Bantam Lake. The house features multiple outdoor decks, large windows, and is surrounded by trees, providing a serene setting. A private dock extends into the lake, inviting exploration.

4.87 out of 5 average rating, 150 reviews

Bantam Lake Waterfront Retreat with Private Beach

Waterfront home on Bantam Lake, 3BR/2BA. Relax on the deck, enjoy the sunrise, swim at your private beach. Kayaks available for use (4); bring your boat or jet ski. Minutes away from hiking, snow skiing, vineyards, biking, and so much more. The area offers great restaurants and family friendly activities that are minutes away. BBQ on the gas grill, enjoy the fire pit on the beach. House is great for couples, individuals & families. Please check first if you plan to bring a boat. 7 maximum.

A charming two-story blue house is framed by lush greenery and a manicured lawn. Soft light emanates from the yellow windows, creating a welcoming glow. A red door stands as a vibrant focal point, inviting guests into the comfortable space.

Home in Litchfield

4.84 out of 5 average rating, 376 reviews

Rustic - Modern - Hot Tub - Mohawk Mountain - BBQ

Enjoy the comfort of home with air conditioning, heating, dedicated workspace, TV, and Wi-Fi. Cook your meals in the fully-stocked kitchen with all the essentials. Pamper yourself in the private bathtub or shower with provided body soap, shampoo and conditioner. Relax in the hot tub or lounge in the backyard with an outdoor dining area, bbq, patio, and fire pit. 3 Min - Litchfield Town 4 Min - Arethusa Dairy farm 5 Min - White Memorial Conservation Center 16 Min - Mohawk Mountain Ski Area

A functional kitchen is equipped with stainless steel appliances, including an oven and microwave. White cabinets provide ample storage, while a granite island offers seating with four high-backed chairs. The open layout connects to a dining area, creating a seamless flow throughout the space.

Home in New Milford

4.88 out of 5 average rating, 188 reviews

Renovated, one level home in an excellent location

Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

Top guest favorite

An aerial view captures the coastal neighborhood, with a sandy beach and clear blue water. The vibrant homes line the shore, featuring varied architectural styles. Lush greenery borders the area, enhancing the sense of tranquility and charm typical of beachside living.

Home in Milford

5 out of 5 average rating, 102 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach, Silver Sands, dining, shops & more, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

A bright living area is displayed, featuring two navy blue sofas accompanied by a patterned area rug. A coffee table sits at the center, surrounded by a cozy armchair. A fireplace is set against one wall, with a television mounted above it, enhancing the communal space.

4.8 out of 5 average rating, 199 reviews

Convenient and Cozy Antique Cape

Adorable little house in Darien CT, with a fireplace in winter and the beautiful local beaches in the summer. Right across from Trader Joe’s and around the corner from route 1 and Interstate 95, the little house is super convenient to local amenities. Probably the best perk of its central location is that it’s nestled behind Rorys, the best pub ever, so there’s no need to even cook if you are too busy or just don’t want to after working all day or a long day at the beach

An open-concept space is seen featuring hardwood floors and natural light. The kitchen includes white cabinetry and modern appliances, while a farmhouse table is surrounded by chairs. Pendant lights hang above the kitchen island, complementing the rustic wooden beam overhead.

Home in Stonington

4.98 out of 5 average rating, 172 reviews

Historic charm & modern luxury in downtown Mystic

We are long-time AirBNB guests who have tried to create the home we are always looking to book -- family friendly with modern amenities. Open floor plan on the main level, new heat and air con throughout the house, three bedrooms and family bathroom on the second floor. Art supplies, toys and children's books all ready for you as well as a pack n play and booster seat. Backyard oasis with pergola, walking distance to drawbridge. Pets considered on a case by case basis.

Top guest favorite

A charming house is visible along the riverbank, surrounded by lush greenery and blooming trees. The landscape features the calm waters of the river, reflecting the clear blue sky dotted with soft clouds, providing a scenic backdrop to the quaint property.

4.99 out of 5 average rating, 111 reviews

Best River View, on Rail Trail in Collinsville!

This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

A bright living area is illuminated by natural light through large windows. A decorative black wall with a welcome message adds character. A comfortable seating arrangement and dining space is featured. Art pieces are displayed, enhancing the creative ambiance of the space.

Home in Montauk

4.99 out of 5 average rating, 101 reviews

6 minute walk to Ditch Plains Beach

IMPORTANT: From Memorial Day 2024 - Labor Day 2024: weekly (1 week/2 week/3 week rentals must start and end on Saturdays. Monthly rentals can start on the first of the month regardless of the day of the week. Great beach house close to Ditch Plains beach with 3 bedrooms and 2 bathrooms. 2 queen beds and 2 bunk beds, deck, barbecue, outside shower, huge yard, recreation room. Spend your days at the beach and grill at night. Wifi, tv, and outdoor fire pit.

A dining room table with eight chairs is set beneath ambient lighting. The room opens to a cozy living area featuring a comfortable sofa and blue curtains. A doorway leads to a well-lit kitchen, enhancing the home's spacious layout.

Home in New London

4.94 out of 5 average rating, 134 reviews

House in NL near CGA, Sub Base, Mohegan Casino

House is located in New London CT. Off I95 near Coast Guard Academy 3 mins, Connecticut College 4 mins, Mitchell 11 mins, Navy Base 9 mins,Yale L&M Hospital 10 mins, Branford House Avery Point 15 mins, Ocean Beach 16 mins, Millstone 19 mins, Mohegan 16 mins, Foxwoods 24 mins, Electric Boat 9 mins. Enjoy private house with full kitchen, and dining room for family get together. 20% Discount weekly stay. 35% on monthly stay

A rocky shoreline is framed by a silhouetted tree against a colorful sunset. Clouds display shades of pink and orange as the sun sets over the water, creating a serene atmosphere. The beach area offers a peaceful view of nature.

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Popular amenities for Middlesex County house rentals

Free parking on premises

Air conditioning

House rentals with a pool

A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.

Home in East Hampton

4.88 out of 5 average rating, 107 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

A modern home is set in a lush green environment, showcasing a spacious heated saltwater pool surrounded by a stone patio. Relaxing lounge chairs are placed alongside the pool, and the house features large windows that reflect the tranquility of the yard.

Home in East Hampton

4.88 out of 5 average rating, 109 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

Top guest favorite

An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.

Home in Cheshire

5 out of 5 average rating, 134 reviews

Pool House

A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.

Home in Litchfield

4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

Top guest favorite

Home in East Hampton

5 out of 5 average rating, 37 reviews

Stunning Central E. Hampton Home w/ gunite pool.

The exterior of a single-story home is presented, featuring a manicured lawn and a symmetrical facade. Solar panels are installed on the roof. Large windows are visible, providing natural light to the interior. A path leads to the front door, flanked by neatly trimmed shrubs.

Home in Montville

4.94 out of 5 average rating, 157 reviews

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos

Top guest favorite

A modern ranch house is set against a backdrop of lush greenery. A large luxury mineral spring pool draws attention, surrounded by a spacious patio with lounge chairs. An outdoor seating area features a covered porch, providing a relaxing space for gatherings.

Home in East Marion

5 out of 5 average rating, 12 reviews

Long Island home w/ large pool

A clear, inviting pool is set within a wooden deck area surrounded by lush mature pine trees. Comfortable lounge chairs are positioned nearby, offering a relaxing space beside the water. A sun umbrella provides shade for those seeking respite from the sun.

Home in East Hampton

4.94 out of 5 average rating, 16 reviews

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

Weekly house rentals

A two-tiered wooden display stands on a dining table, showcasing starfish and decorative stones. The lower section features a painted image of a manatee against a green background, while the upper level displays additional starfish. Natural light illuminates the table's wooden surface.

Home in Westerly

4.94 out of 5 average rating, 18 reviews

Beach House Minutes to relaxing by the ocean

A serene view of Squantz Pond is framed by lush greenery, with vibrant trees and neatly trimmed grass in the foreground. The tranquil water reflects the sky, creating a peaceful atmosphere, while a private dock is visible along the water's edge.

Home in New Fairfield

4.92 out of 5 average rating, 117 reviews

Beautiful Lakefront Retreat with Private Dock

A serene waterfront view captures a gradient sky transitioning from deep blue to vibrant orange and yellow at sunset. The calm water reflects these warm hues, while silhouettes of wooden structures outline the shoreline, offering a peaceful and picturesque setting.

Home in Amagansett

4.93 out of 5 average rating, 14 reviews

Amagansett, Waterfront retreat

The front exterior of the bungalow is showcased, featuring a wooden fence that provides privacy and a garden filled with hydrangeas. The house displays large windows that invite natural light, set against a backdrop of gravel and greenery.

Home in Greenport

4.97 out of 5 average rating, 257 reviews

The Greenport Bungalow

Top guest favorite

A blue bungalow exterior is shown, featuring a spacious deck with black railings and multiple glass doors. A picnic table is situated on the lawn, alongside a children's toy. Lush greenery surrounds the property, enhancing the setting.

Home in Montauk

5 out of 5 average rating, 20 reviews

Montauk beach house!

The spacious patio is shaded by a vine-covered pergola, featuring a round dining table surrounded by black chairs. Lounge chairs are positioned nearby, and the yard extends beyond, showcasing green grass and a variety of plants, contributing to an inviting outdoor space.

Home in Greenport

4.94 out of 5 average rating, 109 reviews

Maritime Village Getaway with Backyard

A balcony view captures a serene beachfront scene at sunset, with gentle waves lapping at the sandy shore. A detailed metal chair is positioned on the deck, providing a quiet spot to enjoy the tranquil waters and cloudy sky.

Home in East Lyme

4.96 out of 5 average rating, 188 reviews

Beachfront Paradise

The spacious living area features wooden beams and natural light streaming through large windows. A light-colored sectional couch is complemented by soft, decorative pillows. Two lamps illuminate the room, while a flat-screen television is mounted on the wall opposite the seating area. White curtains frame the windows.

Home in Madison

4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

Private house rentals

The exterior view of the house is shown, featuring a clean white facade and large glass doors. A spacious deck is visible on the second floor. A wooden bench is positioned on a stone patio, surrounded by well-maintained greenery.

Home in Stonington

5 out of 5 average rating, 3 reviews

Shell House

A spacious backyard features a large swimming pool surrounded by a brick patio. The two-story home, with a screened-in porch and an upper deck, is complemented by lush greenery. A pool house and lounge chairs provide additional relaxation areas.

Home in East Hampton

4.88 out of 5 average rating, 110 reviews

Gorgeous East Hampton Getaway

The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.

Home in East Haven

4.89 out of 5 average rating, 104 reviews

Welcome To Piper's Rest

Top guest favorite

A two-story home features a light-colored exterior with traditional shutters and a welcoming front porch. The yard is neatly landscaped with greenery and flowers. A wooden deck is visible at the back, providing an inviting outdoor space.

Home in Old Saybrook

4.97 out of 5 average rating, 121 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

A charming colonial house displays a white exterior with a dark roof and welcoming front porch. Colorful flower beds with various plants frame the walkway, while a grassy area extends towards the front. A clear blue sky with fluffy clouds complements the serene environment.

5 out of 5 average rating, 14 reviews

Luxury/pool/private Villa Mariana Blackberry River

The estate is set on expansive green lawns, framed by mature trees. The picturesque house features a charming combination of traditional architecture and modern details, with expansive verandas and a large outdoor deck providing ample space for relaxation.

Home in East Haddam

5 out of 5 average rating, 25 reviews

Elegant Countryside Estate

An outdoor patio features multiple wooden lounge chairs arranged around a central fire pit. A gunite pool with clear water reflects the surrounding greenery. The main house, visible in the background, showcases a classic design with white siding and large windows.

Home in Sag Harbor

4.86 out of 5 average rating, 263 reviews

Exclusive Sag Harbor Compound

A modern kitchen features sleek black cabinetry and stainless steel appliances. A large island with bar seating is centered, adorned with a vase of fresh flowers. Natural light floods in through the windows, and a sliding glass door leads to the outdoor deck.

4.92 out of 5 average rating, 330 reviews

Stunning, peaceful and private home

Destinations to explore