Guest house holiday rentals in Middlesex County

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Top-rated guest house rentals in Middlesex County

Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

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Top guest favourite

A charming cottage features wood shingle siding and a neatly arranged entrance. The front yard showcases a manicured area with green grass, accompanied by a duck and a chicken. Nearby, expansive fields and a rustic barn complete the serene rural landscape.

Guest house in Portland

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.

4.98 out of 5 average rating, 351 reviews

Superhost

A cozy bedroom features a queen bed with a light blue quilt and a green loveseat nearby. Natural light enters through sliding glass doors, revealing a serene outdoor space. A decorative plant and framed artwork add a touch of interest to the room.

Guest house in East Hampton

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

4.82 out of 5 average rating, 349 reviews

Guest favourite

A spacious living area is presented with a large flat-screen TV mounted on a white entertainment unit. A soft gray sofa sits nearby, and a decorative area rug enhances the room's aesthetic. Natural light streams in through a front door adorned with a glass panel.

Guest house in Watertown

Private studio guesthouse

Kick back and relax in this peaceful, quiet, stylish space with high ceilings, central heat and air, huge bathroom, mini kitchen, fridge, microwave, coffee maker, 75" TV, onsite laundry and workout equipment when needed, private parking space, private entrance, high-speed internet, countless local restaurants, fast food chains and cafes, all major supermarkets, hospitals and doctors offices, post offices, easy access to numerous lakes, golf course and wineries. Indeed, a home away from home.

4.93 out of 5 average rating, 122 reviews

Top guest favourite

The exterior of a bright red carriage house is surrounded by lush gardens filled with various flowers and greenery. Two large windows and a white door are visible, adding charm to the traditional New England design. A well-maintained lawn complements the vibrant landscape.

Guest house in Wallingford

The Garden Loft - A Charming New England Stay

Welcome to The Garden Loft! Located in the heart of downtown Wallingford, CT. This traditional and historic New England carriage house has been completely renovated in the summer of 2022 into a peaceful, cozy, bright & airy loft. We are a 3 minute walk from downtown where you will find a variety of restaurants, bars, a brewery & only 1 mile from from Choate Rosemary Hall. A 15 minute drive to Yale University & downtown New Haven. Get ready to relax, get cozy & enjoy The Garden Loft!

5.0 out of 5 average rating, 170 reviews

Top guest favourite

A light-filled living space features two skylights allowing natural light to illuminate the wooden floors. A spacious sofa is accompanied by a small coffee table and a seating area is positioned beside a contemporary television. Potted plants add a touch of greenery to the room.

Guest house in Milford

The studio downtown

The studio is a new, private, quiet, and peaceful space. It is situated on the second floor of a detached garage with a private entrance. It is located in the historic center of town, within walking distance of the train station, bars, restaurants, and beach. It is ideal for a couple looking for a beach town getaway. The studio has a king-size bed, an eating area, a kitchenette with a fridge, a sink, a double induction cooktop, a seating area, and a bathroom with a rain shower.

4.99 out of 5 average rating, 107 reviews

Top guest favourite

A tranquil section of the Little River is depicted, featuring cascading water creating gentle ripples. Sunlight reflects off the surface, enhancing its natural beauty. Lush green leaves frame the scene, adding a touch of nature to the flowing water.

Guest house in Sprague

House on Little River / Writer Retreat

Rustic cottage on on Little River, a lovely trout stream that swishes around rocks. Great place for kids to play! Lake across the street. Canoe. Woods all around. Very quiet except for hush of river. Nice deck extends almost to the river. Gas and charcoal grills. In all ways cozy and pleasant. Nice for couples, writers, artists, travelers, families, and pets—a place for quiet, peaceful people. About the lake: There's no beach. Access is just a narrow path down to the water.

4.96 out of 5 average rating, 214 reviews

Top guest favourite

The exterior of a private guest house is depicted, showcasing a blue facade complemented by multiple windows. A spacious stone patio features outdoor seating surrounded by lush greenery and garden flowers. The roof is sloped, and trees provide a natural canopy overhead.

Guest house in Guilford

Page Guest House

Updated, private detached guest house in the center of Guilford's historic district just steps from the town center. The guest house is completely renovated. Walk to everything including shops and restaurants. Town Beach and doc are just under 1.5 miles away. The second bedroom has a twin bed. You have to walk through twin room to get to master. Apartment is one floor with no steps. Bathroom is tiled and shower is walk in with no lip or tub and is easily accessible.

4.98 out of 5 average rating, 114 reviews

Guest favourite

A charming cottage exterior features white clapboard siding and dark blue shutters. A sloped asphalt roof and a front door with decorative glass provide focal points. Landscaped greenery and a gravel pathway enhance the welcoming entrance, surrounded by trees that offer natural shade.

Guest house in Clinton

The Gardener's Cottage Dog friendly/weekly/monthly

The Gardener's Cottage, less then a mile from the Long Island Sound, is a great alternative to the common hotel. Situated a stones throw from Hammonasset State Park and Beach, Clinton Outlets, and the Shore Line East train station. Near by you will find places to kayak, Chamard Wineries, Marinas and many quaint New England towns. The Cottage is fitted with it's own router coupled with an eating nook that can double as a work space. Pets are allowed. Self check-in

4.94 out of 5 average rating, 253 reviews

Top guest favourite

A modern living space features a comfortable sofa, a circular coffee table, and a television unit. Large sliding glass doors create a seamless view of the outdoors, with natural greenery visible beyond the private deck. Soft natural light fills the room, enhancing its inviting ambiance.

Guest house in Guilford

Get Back to Nature at a Modern Wood Clad Getaway

Catch the early fall breeze at our private coastal cottage. Spot migrating shorebirds, terns, and early warblers. Beautiful hiking trails in the woods and along the beachfront. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Great restaurants along the shore. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

4.99 out of 5 average rating, 527 reviews

Guest favourite

A cozy living area features mid-century modern furniture, including an orange armchair and a sleek glass coffee table. A gallery wall displays various artworks, complemented by natural light from two windows. A small dining area with a round table and four chairs contributes to the inviting layout.

Guest house in New Haven

Westville Hideaway | Stylish Guesthouse + Parking

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. A serene private guesthouse perfect for couples, creatives, and travelers. Stylishly decorated with modern amenities, this space is a cozy retreat just a short walk to Westville Village and Edgewood Park. Ideal for weekend getaways, local visitors, or professionals seeking a quiet base with fast WiFi and free parking.

4.92 out of 5 average rating, 354 reviews

Guest favourite

A spacious barn is situated in a large field, surrounded by greenery. Its two-story structure features a combination of windows and a central door, offering access to the outdoors. Lush grass and various plant life contribute to the serene rural setting.

Guest house in Hampton

Spacious, unique barn with beautiful views.

Our barn is in a large field on lot next to our home. Our rental area is upstairs which offers beautiful views of our field and the visiting deer. The eclectic decor is accumulated from years of activism. Our guest room and bathroom are newly renovated. It is a quiet and peaceful area near two state parks. We operate a mail order business in the downstairs area but will not be working while guests are staying with us.

4.95 out of 5 average rating, 176 reviews

Top guest favourite

Natural light fills the bright living area, featuring a comfortable seating arrangement with decorative cushions, a wooden coffee table, and an elegant antique cabinet. High ceilings with exposed beams enhance the spaciousness, complemented by large windows offering views of the greenery outside.

Guest house in Madison

Beachy & Bright Coastal Escape - 5 Mins to Beach

Charming coastal guesthouse in Madison’s historic district—just a 5-min walk to a private beach, 5-min drive to town, and 20 mins to New Haven. Bright, beachy, and newly renovated with a king bedroom, full kitchen, private deck, and huge backyard. Set on nearly an acre in the heart of New England, it’s perfect for couples, families, and girls’ getaways. Walk to cafes, shops, and the iconic RJ Julia bookstore.

4.97 out of 5 average rating, 126 reviews