
Guesthouse vacation rentals in Middlesex County
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Top-rated guesthouse rentals in Middlesex County
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Popular amenities for Middlesex County guesthouse rentals
Family-friendly guest house rentals

A Comfy Hilltop Home
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.

Private room w/ private bath - single family house
Everything was great about the room, as it was comfortable and spacious. The location is very good, as it's a 10-minute walk from the metro station, and the surrounding area feels safe and quiet. There are also many shops and restaurants nearby. On the day of my arrival, Jane had left a banana cake in the room, which was a great detail

Country Cottage in the City
What a perfect weekend in a private cottage by the pool. Although the weather did not cooperate for pool time, Mark & Susan’s cottage was a perfect place to have a central location outside of Boston. You would never know you were close to the city. Absolutely lovely! Their cottage was super clean and inviting and lacked nothing necessary for a long weekend away. They were very proactive in communicating with us about checking in and if we needed anything during our stay. Really terrific!

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

Dream Inn LLC Rm2 Fitchburg Free WiFi & Parking
They are very friendly and answered any questions that I had and they are also very accommodating.i highly recommend them

Jimmy & Donny's AirBnB
If I could give 10 stars I would! The place was super cozy, and beautiful. We were given great recommendations for the area and destinations we were seeing in Boston and Salem. They made my wife’s 30th birthday one she’ll never forget! The muffins were fantastic and the fresh fruit made every day start off wonderful. I highly recommend coming here if you’re looking for a peaceful, beautiful and relaxing time in Massachusetts. :)

Cozy One Bedroom Private Unit - Prime Location!
I had a fantastic stay at Ruben’s place. The apartment was modern, cozy, and very private. The quiet neighborhood felt safe, and it’s only about 20 minutes from Boston. The backyard was beautiful, and Ruben was warm and welcoming. His playful little Pomeranian was a sweet touch, and there were no noise issues at all. Check-in was smooth, and Isabella, the co-host, was great with communication. I’d definitely stay here again!

Peaceful Studio | King Bed, Full Kitchen, Deck
Guest house rentals with a washer and dryer

Private Studio Guest House w/ Free Parking
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 🙏🏼

The Pool House at The Acropolis
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.

Charming 1880 Historic Carriage House
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

Lovely & Spacious 2 BR (W/King/Queen beds) 2 Bath
I had a great stay! The couches were especially comfortable and featured convenient power controls. The kitchen was a perfect size—well-equipped with all the appliances working flawlessly. I easily found all the utensils, plates, cups, and everything else I needed for cooking and dining. The variety of lighting options, including several lamps and switches, made it easy to create the right mood in every room. Would definitely stay again.

Modern, Cute 2 BR Carriage House North of Boston
My two young children and I had to do a last minute trip up to Boston for a loved one’s funeral. Our original sleeping arrangements were not ideal for young babies and then I came across samatha and John’s bnb, I knew I had to book. I’m so glad I did. The stay was very clean, well thought out, uncluttered, functional, no weird smells and most importantly comfortable. My oldest kept asking every time we went out if we were going back to the bnb because it’s so fun. They were very accommodating and easy to communicate with. We would absolutely book with them again next trip up.

Sunny 1BR w views, close to BC and Boston
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.

Carriage house outside Cambridge
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.

Beautiful Cambridgeport Apartment (Central Square)
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!
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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
- Freedom Trail
- Faneuil Hall Marketplace
- Roger Williams Park Zoo
- Crane Beach
- Prudential Center
- Canobie Lake Park
- Good Harbor Beach
- MIT Museum
- Rye North Beach
- Bear Brook State Park
- Wentworth by the Sea Country Club
- Museum of Fine Arts, Boston
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