Guesthouse vacation rentals in Middlesex County

Find and book unique guesthouse rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Middlesex County guesthouse rentals

Family-friendly guest house rentals

Superhost
A bright living area is highlighted by large windows offering expansive views. A comfortable sofa and a futon are arranged around a round coffee table. Light-colored walls and hardwood flooring contribute to the serene ambiance of the space.
Guesthouse in Shrewsbury
4.73 out of 5 average rating, 228 reviews

A Comfy Hilltop Home

DeniseRating, 5 stars5 days ago
From making the reservation to checkout Jason was very communicative. Check in was easy, place was spotless and it had everything you would need for an extended stay. Our stay was from Sunday to Friday. Very peaceful and great place to work from. Beds were comfy. Restaurants and local grocery stores were all within a 10-15 minute drive. Everything was very accessible. Would definitely stay again if we were in need for a place in the area. Highly recommend.
Guest favorite
A cozy sleeping area is featured with a spacious bed adorned with a colorful quilt. Natural light filters through multiple windows, highlighting the wooden trim and a comfortable sofa nearby. A small side table and an antique cabinet add charm to the room.
Private room in Somerville
4.95 out of 5 average rating, 228 reviews

Private room w/ private bath - single family house

MadelynRating, 5 stars2 weeks ago
This was a lovely room, with its own mini fridge and coffee maker. The hosts were so kind and friendly. I would definitely reccomend this space. Their garden is beautiful as well!
Top guest favorite
A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.
Guesthouse in Dedham
4.95 out of 5 average rating, 196 reviews

Country Cottage in the City

JulieRating, 5 stars1 week ago
Beautiful setting in the woods, incredibly peaceful- yet minutes away from a lovely New England village with shops and cafes.
Guest favorite
A driveway paved with red bricks leads to a garage with black doors, situated at the front of a duplex building painted in soft yellow and accented with black trim. Bright sunlight illuminates the scene, highlighting the inviting exterior.
Guesthouse in Boston
4.89 out of 5 average rating, 62 reviews

Airy new apt for 2-6. Near subway. Free parking.

DenessaRating, 5 stars2 days ago
Woody and Pauline are fantastic hosts and their beautiful apartment was the perfect home-base for our recent trip to Boston. The T is really only a block and a half away and you can access all of Boston from the T. Jamaica Plain is adorable and there’s lots of beautiful green spaces nearby. JPizle was fantastic and Evergreen Coffee was also good. Both within easy walking distance. Everyone is super friendly. If you are not familiar with the streets, it can be really hard to navigate getting to the house from the interstate or back again. A tiny neighborhood Whole Foods is a 6 minute drive away. The bedroom downstairs was a little stuffy for us, but we just moved the fan from upstairs down and Pauline said it was okay. Otherwise we were very comfortable and really enjoyed our stay. The antique furniture was lovely, the space was spotless, and the location was perfect!

Guest house rentals with a washer and dryer

Top guest favorite
The entrance to the studio guest house is highlighted by green siding and white trim. A welcoming door with a decorative glass insert sits beneath a gently striped awning. Lush hostas and decorative stones line the walkway, enhancing the outdoor space.
Guesthouse in Boston
4.93 out of 5 average rating, 42 reviews

Private Studio Guest House w/ Free Parking

MarcRating, 5 stars3 weeks ago
James was a great host and his space was a perfect location. Close to the city but not too close. He was friendly and communicative. I would definitely stay with him again. Namaste 🙏🏼
Top guest favorite
A charming cabin exterior is illuminated softly at night, featuring wooden shingles and a welcoming porch. Bright windows allow glimpses of the interior, while an American flag stands proudly on display. Lush greenery surrounds the entrance, enhancing the cabin's rustic appeal.
Private room in Billerica
4.95 out of 5 average rating, 109 reviews

The Pool House at The Acropolis

TianaRating, 5 stars2 weeks ago
We loved staying here, it felt very private. Stephen does a great job at maintain professional boundaries while still being amicable and friendly. Restroom was very clean and the pool house was comfortable to sleep in.
A landscaped backyard is featured, showcasing a stone patio with white Adirondack chairs arranged around a small table. Lush green grass and garden beds with various plants and flowers surround the area. Tall pine trees stand in the background, contributing to a serene atmosphere.
Guesthouse in Westford
4.99 out of 5 average rating, 98 reviews

Charming 1880 Historic Carriage House

LisaRating, 5 stars1 month ago
We had such a wonderful stay at Coby's carriage house. Coby was the ultimate host and can't say enough good things... would definitely recommend staying here if you have plans to travel to the Boston area, excellent location. Linda, Lisa
Guest favorite
The entrance to the Windsor Carriage House is framed by a welcoming archway, featuring a decorative sign and potted flowers. A brick pathway leads to the door, with greenery lining the sides and glimpses of the neighboring structures visible in the background.
Guesthouse in Melrose
4.99 out of 5 average rating, 85 reviews

Modern, Cute 2 BR Carriage House North of Boston

BrianRating, 5 stars2 weeks ago
This place is a gem. Walkable to the Orange Line or a two minute drive with very affordable parking at the T station. It would have been an easy drive but with the T so close….why not use it?! The house is clean, spacious and was great for our family of 4. Melrose itself offers a lot so there’s just so many nice options close by. Will stay here again.
Top guest favorite
A private terrace is shown with a small glass table, two chairs, and a scenic view of the surrounding area. A plate with pastries and a coffee cup is placed on the table, framed by blooming flowers and the distant skyline on a cloudy day.
Guesthouse in Newton
4.99 out of 5 average rating, 81 reviews

Sunny 1BR w views, close to BC and Boston

JacobRating, 5 stars1 week ago
We stayed at Mary and Dave’s place for a week for my wife’s graduation. We absolutely loved the place - it was clean, peaceful, adequately spaced and had spectacular views. They even had toys, books and a play structure which my three year old daughter absolutely loved. Mary and Dave were gracious hosts and were very kind and helpful in their communication with us. We would definitely look to stay again when we visit Boston. Highly recommend staying here. Thanks again for hosting us, Mary/Dave.
Top guest favorite
A modern kitchen features sleek cabinetry and stainless steel appliances. A two-person bar with white stools is positioned at the counter, and natural light filters in through a door leading to the outdoor area. Soft lighting enhances the space, creating an inviting cooking environment.
Guesthouse in Lincoln
5 out of 5 average rating, 15 reviews

Carriage house outside Cambridge

AndreaRating, 5 stars3 weeks ago
Our stay at Benjamin‘s place was great. The location was perfect for us and we enjoyed the whole house. It was very well furnished, very clean and very nice remodeled. I liked the modern kitchen the most. Finally a kitchen well stocked with more then 4 plates and mugs etc. Coffee and tea was provided what was very appreciated. We arrived after a longer drive and could enjoy a cup of coffee right away These are little things but for us these little things mean a lot to us. Communication with Benjamin was great. All in all a perfect stay for us.
Superhost
The entryway of the modern apartment is shown, featuring a wooden door with glass panes beside a garage door made of wooden slats. Potted greenery is positioned next to the entrance, and a concrete driveway is visible with scattered leaves.
Guesthouse in Cambridge
4.91 out of 5 average rating, 44 reviews

Beautiful Cambridgeport Apartment (Central Square)

JuliaRating, 5 stars2 weeks ago
This was my second stay here and it was even nicer than the first time. They had added some thoughtful touches between my visits. I'm hoping to return again this Fall. Many thanks for another wonderful visit!
A narrow entryway is presented with a mixture of materials, including a stone wall alongside a wooden door. A white door on the right leads to a staircase. Natural light from the upper levels subtly illuminates the space.
Guesthouse in Lexington
4.72 out of 5 average rating, 219 reviews

Unique Loft/ Studio Guesthouse (super convenient)

RoddRating, 5 stars3 weeks ago
A lovely upstairs loft studio. Wood floors and tons of natural light, comfortable bed. Small but nice bathroom with various and sundry toiletries. Open kitchen with beautiful view to the back woods, with a lovely private deck with table and chairs. Birds, trees, you feel like you’re having morning coffee in an arboretum! Highly walkable, two level blocks to the main business blocks of historic Lexington - shops, the Battle Green, wine stores, cafes. The neighborhood is one of large, beautiful old homes. An amazing public paved foot and bike path runs 7 miles each way from Lexington, two minutes from the loft.

Destinations to explore