
Guesthouse vacation rentals in Middlesex County
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Top-rated guesthouse rentals in Middlesex County
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Superhost

Guesthouse in Shrewsbury
4.73 out of 5 average rating, 228 reviewsA 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

Private room in Somerville
4.95 out of 5 average rating, 228 reviewsPrivate 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

Guesthouse in Dedham
4.95 out of 5 average rating, 196 reviewsCountry 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

Guesthouse in Boston
4.89 out of 5 average rating, 62 reviewsAiry 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

Guesthouse in Boston
4.93 out of 5 average rating, 42 reviewsPrivate 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

Private room in Billerica
4.95 out of 5 average rating, 109 reviewsThe 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.

Guesthouse in Westford
4.99 out of 5 average rating, 98 reviewsCharming 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

Guesthouse in Melrose
4.99 out of 5 average rating, 85 reviewsModern, 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

Guesthouse in Newton
4.99 out of 5 average rating, 81 reviewsSunny 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

Guesthouse in Lincoln
5 out of 5 average rating, 15 reviewsCarriage 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

Guesthouse in Cambridge
4.91 out of 5 average rating, 44 reviewsBeautiful 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!

Guesthouse in Lexington
4.72 out of 5 average rating, 219 reviewsUnique 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.
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- Hampton Beach
- Boston Common
- Revere Beach
- Fenway Park
- TD Garden
- Harvard University
- Lynn Beach
- Duxbury Beach
- Brown University
- North Hampton Beach
- New England Aquarium
- Monadnock State Park
- Faneuil Hall Marketplace
- Freedom Trail
- Crane Beach
- Canobie Lake Park
- Roger Williams Park Zoo
- Prudential Center
- MIT Museum
- Good Harbor Beach
- Rye North Beach
- Museum of Fine Arts, Boston
- Bunker Hill Monument
- Quincy Market
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