Guesthouse vacation rentals in Middlesex County

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Top-rated guesthouse rentals in Middlesex County

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

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Guest favorite

Guesthouse in Essex

4.81 out of 5 average rating, 27 reviews

Privateers Boathouse (Village Waterfront)

Right in the middle of everything Essex Village has to offer. Very special little waterfront cottage with unrivaled views & access to town is hosting guests. Park your car off-street and enjoy all the wonders of Essex Village by foot during your visit. Secluded, yet utterly central Village location. Short drive to beaches, golf, hikes & more. 🌟 Request a WEEKLY rate 🌟 🛶 Access to swimming pool ONLY WITH ADVANCE ARRANGEMENT 🚣‍♀️ (No onsite kayaks/launch)

Superhost

Guesthouse in East Hampton

4.87 out of 5 average rating, 52 reviews

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

Guest favorite

Guesthouse in Chester

5 out of 5 average rating, 58 reviews

Delightful Cottage in Charming Chester

Enjoy all the Connecticut River Valley has to offer and use this newly renovated cottage as your relaxing home base. The cottage is a 2 min. drive (or 12 min. walk) to charming downtown Chester. There you will find delicious dining options, unique shops, galleries, a brewery and a theater. Chester is also home to a wonderful Sunday farmers market -mid June to mid October. Area attractions include Gillette Castle, Essex Steam Train, Florence Griswold Museum, CT River Museum and wonderful hiking.

Guest favorite

Guesthouse in Clinton

4.96 out of 5 average rating, 23 reviews

Studio Cottage

Peaceful & centrally located studio cottage on Connecticut shoreline. Close to beaches, restaurants, winery, outlet shopping, and I-95. Approximately 20 minutes outside of New Haven. Ideal for exploring the shoreline & river valley. Bright, clean, efficient, well- equipped cozy studio cottage with queen bed, sitting area, kitchen & full bathroom . Outdoor space with fire pit & grill. Onsite parking. Ideal for two people whether traveling through the area or for a little rest & relaxation

Guest favorite

Guesthouse in Old Lyme

4.98 out of 5 average rating, 52 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

Guesthouse in Guilford

4.99 out of 5 average rating, 91 reviews

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.

Guest favorite

Guesthouse in Madison

4.97 out of 5 average rating, 94 reviews

Beachy & Bright Carriage House/5 min walk to Beach

Beach lovers dream. Quintessential New England. This is a one a one of a kind, beautiful & spacious property. If you’re looking for a romantic weekend, girls getaway or a kid friendly space, you have found the perfect spot! Beach is 5 min walk, backyard is a kids paradise, two min drive to town. Antique shops, wineries, seafood restaurants all within 10 mins. Sit on private deck sipping coffee/wine and watch the sun rise or set. Hiking/biking/walking trails right out your front door.

Guest favorite

Guesthouse in Portland

4.99 out of 5 average rating, 146 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Guest favorite

Guesthouse in Essex

5 out of 5 average rating, 34 reviews

Adorable 2 bedroom guesthouse in Essex village

Enjoy the best of both worlds with this remodeled 2 bedroom and 1 bath antique home located on the coveted North Main Street in Essex Village. You are close enough to walk downtown but away from the hustle and bustle. The park-like back yard with an antique trolley bridge and Falls river running through it will give you the perfect place to unwind after a day of activities. Come see why Essex was named “The Perfect Small Town" in the book 1000 Places to See Before You Die!

Guest favorite

Guesthouse in Guilford

4.99 out of 5 average rating, 81 reviews

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.

Guest favorite

Guesthouse in Clinton

4.94 out of 5 average rating, 213 reviews

The Gardener's Cottage Dog friendly/ weekly/montly

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

Guest favorite

Guesthouse in Madison

4.99 out of 5 average rating, 71 reviews

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.