House holiday rentals in Middlesex County

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Middlesex County

House rentals with a pool

Guest favourite
Home in North Andover
4.94 out of 5 average rating, 157 reviews

Nana-tucket Inn

AdamRating, 5 stars2 weeks ago
The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.
Top guest favourite
Home in Newton
5 out of 5 average rating, 18 reviews

Villa with private Pool in Boston's Elite Enclave

BrandonRating, 5 stars3 weeks ago
We stayed for a graduation for our son and the house comfortable accommodated our entire family including parents/ in-laws. There was a creek in the back, pool, Firepit. We had fun playing pool (billiards) and darts. Nice Kitchen with new appliances. The 3 bedrooms are nice in size and we never felt cramped accommodating us all. The host communicated very quickly and was sooo nice. We unfortunately won’t be in Boston in near future however if we did and needed the space we would book again.
Guest favourite
Home in Worcester
4.96 out of 5 average rating, 101 reviews

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

XufengRating, 5 stars2 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! 💛
Top guest favourite
Home in Arlington
4.94 out of 5 average rating, 34 reviews

Beautiful Spacious 4BRM House!

NicholasRating, 5 stars1 week ago
I loved everything Maxine said and how she helped navigate around every even in the house, everything was so clean, very quite place good for professional working, everything was just beyond, amazing & lovely place you feel right at home with so much space to move around the house. Being free having your privacy. Thank you Maxine 🙏👏🏽
Top guest favourite
Home in Norwood
4.95 out of 5 average rating, 44 reviews

the house of id; vintage shop, accessible space

JasonRating, 5 stars3 days ago
Super fun and eclectic house! What really made the stay were the owners, they are thoughtful and very responsive, they clearly care a lot about their guests!
Guest favourite
Home in Weston
4.97 out of 5 average rating, 94 reviews

Spacious vacation unit in premium suburban town

JenniferRating, 5 stars1 month ago
I had a wonderful stay at this Airbnb in Weston, MA. The house was spacious, spotless, and located in a peaceful, wooded neighborhood right next to Cat Rock Park—perfect for relaxing or enjoying nature. It was incredibly quiet, which made for a restful stay. Parking was convenient, and check-in was seamless. Everything about the experience was easy and comfortable. I would absolutely recommend this place to anyone looking for a clean, quiet, and well-located home away from home.
Superhost
Home in Canton
4.88 out of 5 average rating, 25 reviews

Hidden Gem near Boston w/ Private lake access

RachaelRating, 5 stars4 weeks ago
Absolutely incredible stay. The host was very helpful. The house is absolutely beautiful, and the lake is stunning. The basement was so so fun- darts, ping pong, billiards, and more games. We miss the house already!
Guest favourite
Home in Waltham
4.9 out of 5 average rating, 50 reviews

Quiet/Private Neighborhood

ElmerRating, 5 stars4 days ago
Hands down one of the best Airbnbs my family and I have stayed in! We didn't want to leave this place. To top it off, Michelle is a great host. 5/5 rating for sure!

Weekly house rentals

Top guest favourite
Home in Wellesley
5 out of 5 average rating, 40 reviews

Elegant Guest suite Wellesley

CesarRating, 5 stars2 weeks ago
It was my second stay here and the whole experience was outstanding, once again. Such a great place and hosts.
Top guest favourite
Home in Chelmsford
5 out of 5 average rating, 18 reviews

* * Crooked_Spring_Colonial * *

LoriRating, 5 stars4 weeks ago
The home is beautiful, exactly as pictured on the site, located on a very quiet street in a wooded area. Very clean, with access to a whole array of kitchenware and other items around the house. Excellent, detailed set of instructions for the home with info on TV controls, gaming system, thermostat control, local recommendations, and departure instructions. This would be an amazing house to stay with small children, as there is a fun playroom with toys in the basement and a great backyard. It's about 45 minutes to Boston without traffic, and about 1 1/4 hours at peak times, so plan accordingly if you are planning travel to downtown Boston. Great local ice cream place just down the street and local shopping about 10 minutes away.
Guest favourite
Home in Westminster
4.97 out of 5 average rating, 70 reviews

Our Pondside Cabin

DanielleRating, 5 stars4 weeks ago
We had a great stay. It really is minutes away from hiking trails, as well as some restaurants. It was exactly what our large group needed. We were able to prepare meals in the kitchen and ate and played board games at the large dining table. The living room area was comfy and large enough for our group to all hang out in. The place was clean and as pictured in the listing. Kathleen was also very responsive to a few questions I had while there. I'd be happy to return.
Guest favourite
Home in Sudbury
4.93 out of 5 average rating, 57 reviews

Historic Victorian Home - Family + Pet Friendly

AlyssaRating, 5 stars2 weeks ago
Matthew's place was a great spot for our big group. Excellent value for the price. Easy communication and clear instructions. We would definitely stay here again!
Superhost
Home in Fitchburg
5 out of 5 average rating, 14 reviews

Feels Home - BBQ, Yard, Fire Pit

LilaRating, 5 stars1 week ago
Hands down the best Airbnb in Mass. walls are clean, no luggage scrapes along the walls. The floors are clean and spotless. The place matches the pictures, there’s no false postings of this home. The hosts are amazing and anytime I’m in MA, I’ll always look for Celia first to avoid bad experiences.
Top guest favourite
Home in Andover
4.93 out of 5 average rating, 29 reviews

Cozy 2 story guest house.

JenniferRating, 5 stars1 week ago
We were delighted to stay at Vanessa’s home, which is even lovelier than the photos depict. The area and home are beautiful and quiet, with all the amenities we needed. We had the opportunity to meet Vanessa, and she was exceptionally kind. Very highly recommend!
Guest favourite
Home in Framingham
4.73 out of 5 average rating, 15 reviews

Very nice home close to Boston

LindaRating, 5 stars3 days ago
The house was perfect. More space than needed for one person. The kitchen was beautifully updated. The mater bathroom looked like it was newly updated. Lots of space, double sinks. The shower had built in places for shampoos and body wash. The mattress in the master bedroom was amazing. The best nights sleep I have had in a long time. Private street was so quiet you could sleep like a log. Jeff checked in to make sure I got in ok and that everything was to my liking. Four Season service and comfort.
Superhost
Home in Framingham
4.85 out of 5 average rating, 85 reviews

Near Boston Beautiful 3 Bedroom in Framingham, MA

ShelleyRating, 5 stars1 week ago
Jim is a friendly and responsive Super-Host. His home suited our needs perfectly. The neighborhood was quiet and safe and it was easy to drive to shops, train station, etc. Thanks, Jim!

Private house rentals

Top guest favourite
Home in Westford
4.74 out of 5 average rating, 87 reviews

Lakefront House with breathtaking sunsets!

TamiRating, 5 stars1 month ago
It’s a beautiful place, in a beautiful area! We had a great time!!
Guest favourite
Home in Fitchburg
4.95 out of 5 average rating, 78 reviews

Guest home in downtown Fitchburg

JasonRating, 5 stars2 weeks ago
The house is very cute. It's obvious when a person cares about what they do, and a lot of care has been put into the property. The host has literally thought of everything a person might need while there. From ample bottled water to amenities that I hadn't even thought of until I saw them here, but that make perfect sense. The host is absolutely delightful, considerate, clear, and kind. When I return to the area, it's likely I'll book the same property based on how great the host is.
Guest favourite
Home in Wayland
4.95 out of 5 average rating, 92 reviews

Spacious 4 bedroom home with large yard

NicoleRating, 5 stars1 week ago
There are not very many AirBandB type places in Wayland, we wanted to stay near family and not have to stay in a hotel. as noted by others, the driveway is short and steep, so have a good parking brake. And the house is close to the road, so in warm weather with windows open there is a lot of traffic noise. The house itself is great. Well appointed with 4 bedrooms and 2 baths for a larger group. Excellent kitchen with a lot of space and the expected appliances. The Keurig machine was appreciated, and the pods that were provided. Nice picnic patio on side of house. We didn't realize the house was divided into 2 rentals (probably our fault for not reading closely), and there were other guests there the whole time, but we never heard any noise; we weren't actually at the house much except to sleep. Great option for the Wayland area!!
Guest favourite
Home in Stoneham
4.94 out of 5 average rating, 54 reviews

Explore Stoneham

PeterRating, 5 stars6 months ago
Stayed here for 10 days in late November. My mom was transitioning from the hospital to rehab and then to her home. I worked all day everyday getting her place ready. John's Place came to be known as My Sanctuary at the end of the day. Very comfortable and very quiet. And John is a very nice, accommodating, compassionate guy. He asked about my mom everyday. I will definitely stay here for my next trip to the Boston area. Thanks for everything, John!
Top guest favourite
Home in Woburn
5 out of 5 average rating, 30 reviews

Large House- 16 mins to Boston + on site parking

HannahRating, 5 stars3 weeks ago
This place was amazing to stay at. It was big enough to accommodate my friends for the Red Sox game we attended nearby. We appreciated the extra amenities and nice touches. The beds were comfy and overall was a great stay. Cannot wait to come back to enjoy again!!
Guest favourite
Home in Berlin
4.9 out of 5 average rating, 20 reviews

Luxurious Spacious Haven Retreat - Close2Boston

MaryRating, 5 stars1 week ago
We were staying in the area for a wedding and Michael’s house was perfect for our family with plenty of room to relax.
Superhost
Home in Sterling
4.94 out of 5 average rating, 32 reviews

Charming lakeside cottage.

SuzanneRating, 5 stars1 week ago
This house on a large pond is a great find! Water views are stellar all day. The driveway has a steep angle but is not a challenge. As with many houses, it has its unique quirks, but the positives are very high. The kitchen is extremely well stocked for cooking or just heat & serve. The furniture is comfortable and functional. We travel for freshwater fishing. With the rowboat, my husband caught & released over 20 fish - all large and small mouth bass. Thank you for sharing your house with us.
Top guest favourite
Home in Framingham
5 out of 5 average rating, 56 reviews

Lake Cochituate Waterfront Home

LeahRating, 5 stars1 week ago
Beautiful private house right on the lake! The house is cozy and clean. So much to do in surrounding areas as well. Amazing hosts very accommodating, extremely friendly, helpful, generous, and respond quickly. Highly highly recommend!

Destinations to explore