Guest house holiday rentals in Middlesex County

Get Back to Nature at a Modern Wood Clad Getaway

WINTER IS HERE…Come and enjoy a wonderful cozy time in our guest house. The winter birds are easy to see and you can still hike along the ocean. Hawks, cardinals, blue jays, bluebirds, gold finches and more are here year round. 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.

Your Own Barn Loft Suite Among the Treetops

Forget your worries in this spacious and serene space. You’ll arrive through your own driveway, park in your own spot and enter through a private entrance. Make yourself at home whether a weekend get away or traveling for work you’ll feel very relaxed. 250’ from the airline trail, walk or bike right into downtown East Hampton for a coffee in the morning or set out on the 30 + mi trail to enjoy your true country getaway. Head into Middletown to enjoy many restaurants, bars or clubs. *NOTE PET FEE

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.

New Haven Pizza Cozy Guest House 1 mile to yale

Welcome to our 2 bedroom 1 bathroom peaceful and centrally-located guest house. Located in the heart of New Haven less than 5 min away from Yale Hospital and less than 10 minutes from Yale University. The unit has some amazing features like a private 1 car parking space and in-unit washer and dryer. The space is cozy, but has all the necessary amenities for a comfortable short or long stay. Full size kitchen appliances, large bathroom with glass shower & central AC. All pizza lovers welcome

Cozy private one bedroom guest apt suite

Centrally located, just minutes from I84, 20 min to Uconn, 15 min to capital of Hartford, 1 hour drive to Cts famous casinos, 30 min to MGM Springfield, enjoy local dining close by. Private entrance guest suite with parking for one vehicle at your door. Private bedroom with double bed and pull out sofa in living room area, workspace, smart tv, internet ready, kitchenette with fridge, microwave, 2 burner cooktop, and coffee maker, snacks and refreshments, linens, some toiletries available

Cozy Guest House Near Trails, Lakes & CT Charm

Enjoy a peaceful retreat in a private guesthouse, located in a rural residential neighborhood, surrounded by the natural beauty of Cockaponset State Forest. -Nearby access to hiking, biking, paddling, snowshoeing, & more -Dedicated work space -Yard with bamboo grove & private patio -Shop, dine, & take in quintessential CT charm at nearby historic towns of Chester & Essex, or foodie Middletown -18 min from Wesleyan University All the comforts of home with the efficiency of living small.

Guilford Lakes Cottage, with hot tub and fire pit.

Kick back and relax in this calm, stylish home, yards from private lakes for kayaking, swimming, fishing or skating in season. For the adventurer, enjoy year round access to extensive forest trail systems for hiking, mountain biking, cross country skiing, and snowshoeing, only a 2 minute walk from our door. Nicknamed " Guilford's Little Augusta," the 9 hole, par 27 executive Guilford Lakes Golf Course is only 1/4 mile away. Five miles south lies one of the 5 most beautiful town greens.

The Garden Loft - A Charming Choate 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!

Cozy Historic Home Guest Suite

Escape to a bright, cozy guest suite next to a historic New England home! Enter through your own doorway and feel welcomed by rich dark‑wood accents and sunlight‑filled rooms. Enjoy a front yard patio, expansive yard, century‑old trees, then local cafés and a state park within a 8 minute drive or an easy day trip by train to Manhattan or Boston. Return to hominess, and modern comforts—Wi‑Fi, kitchenette, queen bed, plus the perk of free private parking. Relax and feel at home.

The Barn by the Sound

Spend a weekend in The Barn: a modern designed free-standing building with guest studio apartment above, designed to look like a barn; the studio has views at tree level of a quiet, old neighborhood; one block from Long Island Sound; on a section of the historic old Boston Post Road. There is lots of natural light coming from a large window with a lovely view of a privet hedge on our property overlooking a park like property across the street.

Square6ix Stylish Guesthouse in Westville

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.

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.