
Holiday rentals with outdoor seating in Middlesex County
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Middlesex County
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Holiday House Rentals with Outdoor Seating

Tiny house experience steps from the water!
Dean's place was amazing! I felt at peace and felt like I was really in the middle of nature. Quiet and very cozy place! I will be back again! Dean is very friendly and communication is quick and easy!

Hopkinton Mass 3+ Bedrooms - Great location!
Brad was very friendly and helpful. Beautiful home!

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace
From the moment we arrived, we felt completely at home thanks to the incredibly warm and welcoming hosts, Tania and Glenn. They went above and beyond to make our stay comfortable, offering great local tips and always greeting us with a smile. Their hospitality truly made a difference. The home itself is absolutely stunning—beautifully designed, impeccably clean, and filled with thoughtful touches that made it feel extra special. Whether we were enjoying a quiet morning coffee or relaxing in the cozy living area after a day of exploring, everything was perfect. This was one of the best Airbnb experiences we've ever had. If you're lucky enough to find availability here—book it! You won't regret it. Thank you, Tania and Glenn, for a truly unforgettable stay! 💛

Absolutely Gorgeous 3 Bedroom Close to Boston
We were very comfortable as a 3 generation family. Thoughtful details and clear instructions were very helpful and appreciated.

All New Private Country Setting (2 Level-No Share)
If you like spacious, spotless, quiet, and comfortable homes that are stocked with all the essentials and situated in a great location, then you'll love staying at this Airbnb. It was a bit too much space for my needs and preferences as I was traveling solo, and I don't need a formal dining room or two living rooms, but the location and comfort level couldn't be beat. The hosts are very responsive. Do make sure you ask them about the heat controls, I never could figure out how to maintain the right temperature for long, but my visit was pretty short and I managed just fine. Pro tip: Don't miss a chance to sample the savory turkey pot pies and many varieties of sweet pies at nearby Out Post Farm.

Luxury Living at its Best in X-Large 8 Beds Estate
This house was perfect for our family and friends. We were a group of 16 and the house meet our needs. We attended an event at Fenway and Gillette Stadium, the location was great. Tom and Marissa were great host and communication with them was easy. We would stay with them again if traveling to this area.

Balsam Retreat
Grace was so easy to work with. Whenever I had a question, she responded quickly and she was eager to make our stay easy and stress- free. The place is immaculate! We were there for a relative's graduation from The Groton School and the drive was quick- and pretty!

Single family home near Tufts,DT Boston,w/ parking
Everything was as advertised. Simple check in and check out. Did not have a laundry list of unnecessary rules. Start to finish was simple.
Apartment rentals with outdoor seating

Light-Filled Luxury Apartment with View
We loved this apartment. It was well appointed with top of the line furnishings and appliances. But what stood out was the charecter and charm of an older home that was well preserved. It was amazing experience. The kids loved the little loft upstairs. We could watch the sunset from our room every day. The little park is right infront of the apparent with the tower which made it feel more spacious. They also had stuff for coffee and a light breakfast which was a nice touch. We would highly recommend

Lovely townhouse apartment minutes from Boston
This was a perfect stay for a concert at Gillette. We were 10 minutes from the T station that brings the event train to the stadium. The town was adorable and very walkable. Everything was clean. Instructions were clear and entering the apartment was easy. Street parking totally manageable. Would stay here again!

Charming Colonial Two BR Basement Apt with Parking
My daughters and their friends stayed in this Airbnb and absolutely loved it. Lisa communicated very well and was super helpful. She even provided them with a portable mattress just incase they needed it. Not to mention she had everything they needed there such as snacks, toiletry items, and even more stuff. They said it felt just like home and was very cozy! The neighborhood was also very beautiful and it was close by to many different places. Thank you Lisa for having and trusting them. I definitely recommend this place to anyone planning to visit Boston!

3rd FL Apt for 1-4 Guests 15 minutes from Boston
Dave was helpful and responsive as a host the entire time.

Huge 1BR w/King Bed near BOS, Salem, Water &Nature
This was a perfect location for going to the US. This Place was beautiful looks exactly like the pictures,Peaceful and very relaxing made me feel right at home. Very responsive and helpful so I give this place a 10/10 everything was just good for me.

🎖The Ashmont Suite | Close to Subway + Downtown🎖
Our stay at Eddie’s home was nothing short of fantastic. An amazing home with beautiful furnishings and rooms, in a brilliant location just a short subway ride away from Boston city centre/downtown Boston. If I can take my family here again I am a lucky man!

800sq ft, 2BR Apartment w/ AC, Laundry, Parking
This is one of the best Airbnbs we have ever stayed in. It was even better than I expected. Karl has thought of everything to make his guests feel at home. Often we stay at places where the furniture/decor all seem second rate. This home was tastefully decorated, and all the amenities were top shelf!

Luxe Serene 1BR 15 min from Boston with Gym & More
Love this apartment. We’ve stayed here several times. Highly recommend!
Condo rentals with outdoor seating

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee
Appreciate Dan and his beautiful place! The roof deck was especially nice for an evening drink. And the snacks and spindrifts were such a lovely and unexpected touch. Thanks for a great stay!

Family Home + Near Downtown + Cool Backyard!
We had a great stay! Quiet, safe neighborhood, easy to get to the city. Lots of space for the six of us to eat and relax together. Beautiful view of the Boston skyline just minutes walk from the place. Comfortable beds and soft sheets too! We also had no troubles parking nearby and leaving our car (for free) for our entire stay.

Bright & Spacious Home in Davis Sq, Somerville
Wonderful, light-filled home! An easy subway ride to Boston. Our family of 6, including two small children, was very comfortable. Cayla was friendly and helpful.

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA
Reda was so wonderful with us!! Extremely communicative and friendly, the apartment is exactly like the pictures and so much better in person. My family & I had a great time in Boston but the apartment was definitely a big highlight. I recommend this place 10/10🩵

Spacious Dorchester Retreat | 2-bdrm condo
We very much liked staying there. It is a nice neighborhood and very close to South Bay shopping mall with many restaurants and easy and convenient shopping. It is also very close to all major attractions in Boston but much quieter environment. Our host, Marian was extremely helpful, proactive and super responsive, the best we have had so far in our trips. I strongly recommend this place to families.

Cozy Entire Unit Condo close to UMASS Lowell
This home was absolutely perfect for our stay! It was clean, spacious, and beautifully decorated. The open layout made it feel very comfortable, and everything was spotless upon arrival. We especially appreciated how well-stocked and organized everything was—from the kitchen to the bathrooms. The host was responsive and welcoming. We’d definitely love to stay here again!

Spacious, cozy home near Boston!
What a gem!! Ana's appartement is amazing. The bedrooms are large with good mattresses and furniture. Kitchen is great too. There is a nice patio to sit on at the back. Ana's house is extrememy clean, cosy and very well maintained, we will definitely stay here again when we visit Boston!

Boston 2Bd Kg&Qn - Harvard MIT Subway w/parking -2
This spot was really great and fun! 10/10 would recommend to anyone who asked.
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- Hampton Beach
- Boston Common
- Fenway Park
- Revere Beach
- TD Garden
- Harvard University
- Lynn Beach
- Brown University
- Duxbury Beach
- North Hampton Beach
- New England Aquarium
- Monadnock State Park
- Faneuil Hall Marketplace
- Freedom Trail
- Canobie Lake Park
- Crane Beach
- Good Harbor Beach
- Prudential Center
- Roger Williams Park Zoo
- MIT Museum
- Rye North Beach
- Museum of Fine Arts, Boston
- Quincy Market
- Bunker Hill Monument
- Things to do Middlesex County
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