Cottage vacation rentals in Middlesex County

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Popular amenities for Middlesex County cottage rentals

Pet-friendly cottage rentals

Top guest favorite
Private room in Hopkinton
4.98 out of 5 average rating, 91 reviews

Cozy cottage in a quiet, lake community

HeatherRating, 5 stars2 weeks ago
I stayed with Nancy to start a new job for a month. Nancy was so helpful and caring. It was so nice to come back 'home' and walk in the woods or to the beach - what a sweet neighborhood. You do have to deal with some quirky things - like the aggressive neighborhood turkeys - but if you care about the environment (reduce/recycle) and enjoy walking/hiking/water sports, this place is for you.
Cottage in Concord
4.64 out of 5 average rating, 47 reviews

Tranquil Waterfront Retreat

LucyRating, 5 stars2 weeks ago
Tranquil spot in a beautiful surrounding area. The views were incredible - the sunset was idyllic! The communication with the host was very clear and helpful as well. Thank you again
Top guest favorite
Cottage in Worcester
4.89 out of 5 average rating, 124 reviews

Unique and Private Cottage in Worcester

ElaineRating, 5 stars2 weeks ago
I didn’t just stay in a cottage—I stayed in a little slice of peace. This place was everything I dream of one day having: cozy, calm, full of good energy. The hosts had such a kind spirit, quick to respond, and made me feel truly welcomed. Everything was spotless, warm, and just… right. I can’t recommend this place enough—it’s a little sanctuary.
Guest favorite
Cottage in Stow
4.95 out of 5 average rating, 171 reviews

White Pine Cottage

NickRating, 5 stars2 weeks ago
Great older lake house vibe. We liked it very much. It worked great for our family of five.

Private cottage rentals

Top guest favorite
Cottage in Winchester
4.95 out of 5 average rating, 66 reviews

The Little House - a Historic New England cottage

AdamRating, 5 stars2 weeks ago
The Little House was very cleaned and had everything needed for a comfortable stay. I was in town for work and the house's cozy atmosphere and view of the pond made it a great place to unwind and relax at the end of a long work day. I felt right at home. I would love to return on future business trips and it would be great to stay sometime for a more leisurely vacation. Highly recommend!
Top guest favorite
Cottage in Millis
4.99 out of 5 average rating, 125 reviews

Windy Knob Farm Cottage - stay on a working farm

NoraRating, 5 stars2 weeks ago
The farm is lovely, the animals fun, and Jen is a great host. We enjoyed the quiet and loved watching the dogs herd the sheep. Better than TV!
Superhost
Cottage in Groton
4.92 out of 5 average rating, 49 reviews

Cozy, 2BR lake-side retreat and outdoor oasis

AdamRating, 5 stars4 months ago
Absolutely beautiful location. Home was very cozy. Love the kitchen! Brian is a great host. Extremely proactive, helpful and gave great recommendations. Neighborhood is quiet and those around are friendly. Definitely recommend staying at this location again. Wish I would have stayed in warmer weather to utilize the property to its full potential.
Cottage in Westford
5 out of 5 average rating, 4 reviews

Just Chill'inn Cottage

JJRating, 5 stars8 months ago
It was exactly what my family was looking for. It was relaxing and private. It allowed us to not feel cramped like a hotel stay, but allowed us to cook and enjoy the relaxing day. If you have a small kid, the golf cart is a must!
Guest favorite
Cottage in Stow
4.95 out of 5 average rating, 171 reviews

White Pine Cottage

NickRating, 5 stars2 weeks ago
Great older lake house vibe. We liked it very much. It worked great for our family of five.
Guest favorite
Cottage in Arlington
4.94 out of 5 average rating, 155 reviews

Historic 1880 Carriage House

JamesRating, 5 stars1 week ago
Nice place to stay in a quiet neighborhood within walking distance of restaurants and shops. For those interested in history, it is right off Massachusetts Ave which is the path the British took towards Lexington and Concord which are short drive away. Also, it is easy to get downtown since the the northern terminus of the metro ("The T") red line is at Alewife and is only a short drive away with plenty of parking in the garage there. The internet was a little slow but that was great because we got to laugh at our teenagers when they complained about it. Otherwise the house was spacious and comfortable!
Top guest favorite
Cottage in Arlington
5 out of 5 average rating, 39 reviews

Charming Waterfront Cottage Near Cambridge/Boston

CindyRating, 5 stars5 days ago
This beautiful cottage is a hidden gem! The views of the pond from three sides of the living room were a calm respite from busy daily life. The owners have put such care into every detail and have spared nothing in terms of thinking of comfort, welcoming, convenience, and pampering. From luxury linens and phone holders to fresh flowers and a welcome basket with a personal note, I immediately felt at home. The kitchen is well stocked and there is plenty of closet storage. Sabrina checked in when I first arrived and was extremely responsive with any question I had. I hope to book again and would highly recommend a stay at this sweet and comfortable place.
Top guest favorite
Cottage in Andover
4.9 out of 5 average rating, 39 reviews

Cute Downtown Andover Cottage w/ Parking and Yard

TylerRating, 5 stars1 month ago
Spent February at Rick's place and was sad to leave. Very close to all Andover has to offer and vary spacious for a long term stay. Would absolutely stay again and recommend to friends that come in town.

Destinations to explore