Guest house holiday rentals in Middlesex County

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Popular amenities for guest house rentals in Middlesex County

Family-friendly guest house rentals

Superhost
Guest house in Shrewsbury
4.73 out of 5 average rating, 228 reviews

A Comfy Hilltop Home

DeniseRating, 5 stars1 week 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 favourite
Private room in Somerville
4.95 out of 5 average rating, 230 reviews

Private room w/ private bath - single family house

SpencerRating, 5 stars1 day ago
Wonderful location, quiet residential neighborhood but close to Porter Square for the bus, subway, and train. Jane and Alan are such gracious hosts as well!
Top guest favourite
Guest house in Dedham
4.95 out of 5 average rating, 196 reviews

Country Cottage in the City

JulieRating, 5 stars2 weeks ago
Beautiful setting in the woods, incredibly peaceful- yet minutes away from a lovely New England village with shops and cafes.
Guest favourite
Guest house in Boston
4.89 out of 5 average rating, 62 reviews

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

DenessaRating, 5 stars1 week 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 washing machine and dryer

Guest favourite
Guest house in Boston
4.93 out of 5 average rating, 43 reviews

Private Studio Guest House w/ Free Parking

AliciaRating, 5 stars2 weeks ago
Cosy and convenient stay with all the amenities we could ask for. A few minutes walk to the red line, giving quick transport connections throughout the city.
Top guest favourite
Private room in Billerica
4.95 out of 5 average rating, 109 reviews

The Pool House at The Acropolis

TianaRating, 5 stars3 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.
Guest house 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 favourite
Guest house in Melrose
4.99 out of 5 average rating, 84 reviews

Modern, Cute 2 BR Carriage House North of Boston

BrianRating, 5 stars3 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 favourite
Guest house in Newton
4.99 out of 5 average rating, 81 reviews

Sunny 1BR w views, close to BC and Boston

JacobRating, 5 stars2 weeks 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 favourite
Guest house in Lincoln
5 out of 5 average rating, 15 reviews

Carriage house outside Cambridge

AndreaRating, 5 stars1 month 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
Guest house in Cambridge
4.91 out of 5 average rating, 44 reviews

Beautiful Cambridgeport Apartment (Central Square)

JuliaRating, 5 stars3 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!
Guest house in Lexington
4.72 out of 5 average rating, 221 reviews

Unique Loft/ Studio Guesthouse (super convenient)

BrandiandJarredRating, 5 stars3 weeks ago
Nice neighborhood, felt safe to walk around and the loft had most of what we needed. We arrived at night on a very dark night & could not tell if we were in the right place because there was no house number visible and the guest house is tucked far back on the property & no lights lights were on at the time. It felt strange not knowing if we were trespassing on the someone else’s property. Thankfully Peter was responsive and turned on light so we could see. If we had arrived in day light it would not have been a problem at all.

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