Holiday rentals with outdoor seating in Middlesex County

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

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Popular amenities for Middlesex County outdoor seating rentals

Holiday House Rentals with Outdoor Seating

Superhost
Home in Wayland
4.78 out of 5 average rating, 492 reviews

Tiny house experience steps from the water!

VerônicaRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Hopkinton
4.95 out of 5 average rating, 155 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

DeanneRating, 5 stars4 days ago
Brad was very friendly and helpful. Beautiful home!
Guest favourite
Home in Worcester
4.96 out of 5 average rating, 101 reviews

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

XufengRating, 5 stars3 weeks ago
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! 💛
Guest favourite
Home in Watertown
4.95 out of 5 average rating, 110 reviews

Absolutely Gorgeous 3 Bedroom Close to Boston

CarolRating, 5 stars1 week ago
We were very comfortable as a 3 generation family. Thoughtful details and clear instructions were very helpful and appreciated.
Top Guest favourite
Home in Holliston
4.97 out of 5 average rating, 87 reviews

All New Private Country Setting (2 Level-No Share)

JenRating, 5 stars2 weeks ago
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.
Superhost
Home in Southborough
4.87 out of 5 average rating, 167 reviews

Luxury Living at its Best in X-Large 8 Beds Estate

PamelaRating, 5 stars1 month ago
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.
Top Guest favourite
Home in Groton
4.96 out of 5 average rating, 45 reviews

Balsam Retreat

Jen ReadRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Medford
4.94 out of 5 average rating, 160 reviews

Single family home near Tufts,DT Boston,w/ parking

BrentonRating, 5 stars3 weeks ago
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

Guest favourite
Apartment in Boston
4.97 out of 5 average rating, 347 reviews

Light-Filled Luxury Apartment with View

MelissaRating, 5 stars2 weeks ago
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
Superhost
Apartment in Dedham
4.84 out of 5 average rating, 187 reviews

Lovely townhouse apartment minutes from Boston

EmaRating, 5 stars1 week ago
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!
Top Guest favourite
Apartment in Medford
4.99 out of 5 average rating, 266 reviews

Charming Colonial Two BR Basement Apt with Parking

MdRating, 5 stars1 week ago
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!
Guest favourite
Apartment in Newton
4.91 out of 5 average rating, 349 reviews

3rd FL Apt for 1-4 Guests 15 minutes from Boston

PeterRating, 5 stars5 days ago
Dave was helpful and responsive as a host the entire time.
Superhost
Apartment in Everett
4.87 out of 5 average rating, 268 reviews

Huge 1BR w/King Bed near BOS, Salem, Water &Nature

AbigaelleRating, 5 stars3 weeks ago
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.
Guest favourite
Apartment in Boston
4.94 out of 5 average rating, 105 reviews

🎖The Ashmont Suite | Close to Subway + Downtown🎖

JohnRating, 5 stars1 week ago
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!
Top Guest favourite
Apartment in Cambridge
4.97 out of 5 average rating, 133 reviews

800sq ft, 2BR Apartment w/ AC, Laundry, Parking

SusanRating, 5 stars6 days ago
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!
Superhost
Apartment in Malden
4.9 out of 5 average rating, 104 reviews

Luxe Serene 1BR 15 min from Boston with Gym & More

DinaRating, 5 stars2 weeks ago
Love this apartment. We’ve stayed here several times. Highly recommend!

Condo rentals with outdoor seating

Top Guest favourite
Condo in Cambridge
4.92 out of 5 average rating, 781 reviews

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

juliaRating, 5 stars1 day ago
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!
Guest favourite
Condo in Boston
4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

RogerRating, 5 stars3 months ago
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.
Guest favourite
Condo in Somerville
4.9 out of 5 average rating, 141 reviews

Bright & Spacious Home in Davis Sq, Somerville

KristinRating, 5 stars2 weeks ago
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.
Superhost
Condo in Boston
4.93 out of 5 average rating, 102 reviews

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA

NayelyRating, 5 stars1 month ago
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🩵
Guest favourite
Condo in Boston
4.97 out of 5 average rating, 110 reviews

Spacious Dorchester Retreat | 2-bdrm condo

EsfandiarRating, 5 stars5 days ago
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.
Guest favourite
Condo in Dracut
4.85 out of 5 average rating, 117 reviews

Cozy Entire Unit Condo close to UMASS Lowell

LucyRating, 5 stars4 weeks ago
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!
Superhost
Condo in Somerville
4.83 out of 5 average rating, 198 reviews

Spacious, cozy home near Boston!

StephaneRating, 5 stars1 week ago
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!
Guest favourite
Condo in Somerville
4.94 out of 5 average rating, 206 reviews

Boston 2Bd Kg&Qn - Harvard MIT Subway w/parking -2

NathanRating, 5 stars5 days ago
This spot was really great and fun! 10/10 would recommend to anyone who asked.

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