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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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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)

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

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.

Guesthouse in Clinton

4.96 out of 5 average rating, 26 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

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.

Guesthouse in Guilford

4.99 out of 5 average rating, 93 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.

Guesthouse in Madison

4.97 out of 5 average rating, 95 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.

Guesthouse in Portland

4.99 out of 5 average rating, 149 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.

Guesthouse in Berlin

4.9 out of 5 average rating, 29 reviews

Cozy, Spacious, Central Getaway

Spacious, cozy getaway. Near many popular events. Welcome to our comfy offering of a home away from home! Off street parking, prvt patio, view of parklike yard. Well lit pathways, arrows, outdoor cameras, alarm system for security/safety. Full kitchen and spacious bathroom. Dedicated workspace. Off rt 5/15 less than 5 minutes from I 84/I 91 festivals, colleges nearby. Dogs on premise but not in your area. Free Wi-Fi, and smart TV for video streaming.. PlS note no cable TV.

Guesthouse in Essex

5 out of 5 average rating, 36 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!

Guesthouse in Guilford

4.99 out of 5 average rating, 83 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.

Guesthouse in East Hampton

4.93 out of 5 average rating, 41 reviews

Family-Friendly Lakeside Cottage

Newly renovated lakeside cottage with stunning views. 2 bedrooms with king beds and a pull out couch, 1.5 bathrooms - 30 second walk to the lake - Fully furnished and equipped - Private rock patio with picnic table and grill - Washer and dryer in unit - Desk for working from home - 2 Kayaks and 2 paddle boards are available for use - Short walk or drive to restaurants, and shops Perfect for romantic getaways, family vacations, or visiting family locally.

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Popular amenities for Middlesex County guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guesthouse in New London

4.97 out of 5 average rating, 106 reviews

Fully Renovated, Ocean Views, Fireplace & Beach

Guesthouse in Milford

4.92 out of 5 average rating, 203 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Guesthouse in Montauk

4.59 out of 5 average rating, 91 reviews

Montauk Heaven, Beach & Woods

Guesthouse in East Hampton

4.9 out of 5 average rating, 192 reviews

Beautiful Airy Barn in Springs

Guesthouse in Barkhamsted

4.88 out of 5 average rating, 96 reviews

Farmington River Carriage House Pleasant Valley CT

Guesthouse in Sprague

4.96 out of 5 average rating, 201 reviews

House on Little River / Writer Retreat

Guesthouse in Groton

4.94 out of 5 average rating, 429 reviews

Quiet studio with sleeping loft and deck

Guesthouse in Shelter Island

4.96 out of 5 average rating, 115 reviews

Waterfront carriage house studio

Guest house rentals with a patio

Guesthouse in Hampton Bays

4.86 out of 5 average rating, 58 reviews

Quaint One-Bedroom Cottage with Private Entry

Guesthouse in Calverton

4.98 out of 5 average rating, 46 reviews

Private Luxe Cottage at Gates of Wine Country

Guesthouse in Norwich

4.94 out of 5 average rating, 36 reviews

Brand new & close to casinos with HOT TUB

Guesthouse in Sag Harbor

5 out of 5 average rating, 15 reviews

Romantic studio cottage; Walk to town

Guesthouse in Rocky Hill

4.92 out of 5 average rating, 13 reviews

Camellia Springs - Solace & Rest

Guesthouse in Mystic

5 out of 5 average rating, 38 reviews

Mystic Bungalow

Guesthouse in Hampton Bays

5 out of 5 average rating, 4 reviews

Hill Coast Cottage: Freshly Renovated

Guesthouse in Pomfret

5 out of 5 average rating, 42 reviews

Cottage in Quiet Corner. Four miles from town.

Guest house rentals with a washer and dryer

Guesthouse in East Hartford

4.5 out of 5 average rating, 16 reviews

ZenVibe Inn

Guesthouse in Shelter Island

4.89 out of 5 average rating, 9 reviews

Stylish Studio Suite on Shelter Island

Guesthouse in Southold

4.91 out of 5 average rating, 53 reviews

Southold- Adorable 1 Bedroom Cottage

Guesthouse in Mount Sinai

4.58 out of 5 average rating, 40 reviews

Great Outdoors Beach, Pool & Cozy Cabin Welcome!

Guesthouse in New Haven

4.76 out of 5 average rating, 49 reviews

New Haven Pizza Cozy Guest House 1 mile to yale

Guesthouse in New Haven

4.94 out of 5 average rating, 282 reviews

Square 6ix

Guesthouse in Waterford

5 out of 5 average rating, 15 reviews

Waterfront Cottage on the Niantic River

Destinations to explore