Vacation rentals in Middlesex County

4.87 out of 5 average rating, 109 reviews

Vacation home in Natick

Private Lakefront with game room/Newly renovated

SamanthaRating, 5 stars3 weeks ago

My family of six was extremely pleased with our stay at Dean’s property. He was incredibly responsive and helpful when I was having trouble making the reservation. The home was exactly as described. Very clean. Plenty of linens and towels. My kids loved the game room. Would definitely stay here again.

4.9 out of 5 average rating, 181 reviews

Home in Westminster

Lakefront, view of ski mtn, fireplace, sauna

EdwardRating, 5 stars2 weeks ago

Really liked the ocation right on the water and great size for us (two adults and 2 kids under 10). It was a quick trip and didnt spend as much time in Tyler's place as we wanted (since we were diving around a bunch visiting family and friends). But would certainly stay again next time we visit the area.

4.98 out of 5 average rating, 193 reviews

Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

ParkerRating, 5 stars1 week ago

We had the best time in Arlington this past week! We came for the Boston marathon. The place was beautiful and the location was perfect. It was close to Boston but far enough out for the peace and quiet. Doug and Hope were the most exceptional hosts. They were accommodating and very responsive. They went above and beyond to make our stay and everything we needed as easy as possible. They were so great and we hope to come back in the future!!

4.92 out of 5 average rating, 37 reviews

Cottage in Westford

Beach & pond cottage ! Westford MA and Boston!

MelanieRating, 5 stars6 months ago

We had an absolute blast on our girls getaway weekend!! The cottage and community were amazing, exactly what we were hoping for and Doug couldn't have been nicer or more helpful. He was always available by text or phone. The cottage was clean, nicely equipped, and a great location!! We will definitely be renting this cottage again on our next trip!!! Thanks for having us... we loved every minute!! 🧙🧙🧙

Top guest favourite

Farm stay in Ashby

5 out of 5 average rating, 16 reviews

The Wellington House

MargeauxRating, 5 stars4 months ago

We had a wonderful stay at Sharon's place! During the winter the location was picturesque with the view of the horses and pond in the snow. The kitchen was well stocked, making it easy to prepare meals during my stay. Sharon was a great host—she was very accommodating and proactive and made sure I had everything I needed. I would highly recommend staying here!

4.97 out of 5 average rating, 151 reviews

Nxt to ocean, 5 min dntwn by T

MarkRating, 5 stars6 days ago

Nice apartment in really good location. So easy to get into town - bus - T - ferry. Also so easy to get to from the Airport. Apartment was very spacious - clean and tidy. Bar with restaurant at end of the street which also did take away. 20 minute walk to large supermarket. There was the facility to leave bags on final day after checkout as flight was late evening which was very helpful. Overall would recommend. Thank you.

4.84 out of 5 average rating, 31 reviews

The Curie-Perfect for Monthly Stays

XuemeiRating, 5 stars2 weeks ago

This apartment is a great find! The location is perfect, not far from Boston, near every colleges for those who come visiting! This apartment building is indeed very new, built in 2021; but also blended in with history, the leasing office/lobby was converted from an old day chapel, pristine, elegant. Very unique Airbnb experience indeed. The small town is full of vibe with various kinds of cuisines, very good for families, young or old. Melissa, the host is super, giving us very detailed information and instructions from parking to checking in, every tiny details she thoughtfully considered. We couldn’t be happier to stay in this apartment. Highly recommended!

Bungalow in North Andover

4.95 out of 5 average rating, 163 reviews

Luxurious Bungalow at Boutique Winery w/ Tasting

KarlaRating, 5 stars3 weeks ago

A lovely place to stay and so wonderful to be able to bring our pups! The hosts were welcoming and they made an extra effort to accommodate a wine tasting with minimal notice (thank you!). Unfortunately we were in the area for a funeral so did not get to relax and enjoy the surroundings as much as we would have liked. As another guest noted - the linens do have a scent. If you are sensitive or have allergies it's something to keep in mind. Also, bathroom and bedroom are on separate floors - not a deal-breaker but a consideration if you need to use it in the middle of the night. Beautiful property!

4.84 out of 5 average rating, 167 reviews

* NEW Listing * A True GEM in South End , Boston!!

GerRating, 5 stars1 week ago

Great spot for marathon weekend. Lovely quiet area with lots of food options. Apartment was ideal for me and only 15min stroll to bag drop on marathon morning. Santo was great, really responsive and helpful. In Boston terms the apartment was good value, just accommodation in Boston generally is really expensive. I hope I can visit again, Boston is a fantastic city and south end is beautiful

Vacation rentals for every style

Get the amount of space that is right for you.

Apartments

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Middlesex County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Middlesex County

Guest suite in Burlington

4.74 out of 5 average rating, 50 reviews

Lovely Two Bedroom Home in Burlington

JohnRating, 5 stars6 months ago

Paul was a gracious host. Friendly, accommodating and undersanding. I'll definitely book again

4.94 out of 5 average rating, 152 reviews

Home in North Andover

Nana-tucket Inn

JeremyRating, 5 stars5 months ago

We had an absolutely wonderful experience staying at this Airbnb! The home was impeccably clean, cozy, and well-stocked with everything we could possibly need. The host's attention to detail was evident in every corner, from the kids' toys to the thoughtful touches like snacks, coffee, and local guidebooks. The location was perfect—peaceful and quiet but still close to shops and restaurants. I especially loved relaxing in front of the fire and enjoying the serene surroundings. The host was incredibly responsive and went above and beyond to ensure our stay was seamless, offering great tips about the area and checking in (without being intrusive). I highly recommend this spot to anyone visiting North Andover or the greater Boston area.

5 out of 5 average rating, 13 reviews

Home in Ashburnham

The Nutty Bird Lakehouse

FinleyRating, 5 stars1 month ago

Such a beautiful spot! Kathy was extremely communicative - everything went smoothly and I did not need anything but she made herself available if I did. The home was clean and had everything needed for a relaxing stay. I hope to be back soon!

4.78 out of 5 average rating, 40 reviews

(42L2) Celtics, Bruins! Lets GO!

ColeRating, 5 stars3 weeks ago

Great for td garden!!! Clean and cute.

4.97 out of 5 average rating, 101 reviews

Guesthouse in Westford

Detached Waterfront Guest House

LauraRating, 5 stars3 days ago

Lovely, peaceful place to stay. The hosts were very friendly and helpful. Just what we needed. We can highly recommend this place. Thanks again for our lovely stay.

5 out of 5 average rating, 20 reviews

Apartment in Fitchburg

Relaxing Poolside Getaway

RebaRating, 5 stars2 months ago

Desiree & Steven’s place is truly a hidden gem. I stayed during the “off season” when the pool and other outdoor amenities were unavailable, and yet it still felt like retreat even in the dead of winter! It was a particularly snowy time, and Steven always made sure the walkway was shoveled and salted and really went above and beyond to make my stay feel comfortable. When I needed to extend my stay, Desiree and Steven made the process seamless. Truly a hidden gem with the added benefit of outstanding hosts!