
Cottage vacation rentals in Middlesex County
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Top-rated cottage rentals in Middlesex County
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Popular amenities for Middlesex County cottage rentals
Cottage rentals with a hot tub
Superhost

Cottage in Westford
4.92 out of 5 average rating, 37 reviewsBeach & 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!! 🧙🧙🧙

Cottage in Westford
5 out of 5 average rating, 4 reviewsJust 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!
Pet-friendly cottage rentals
Top guest favorite

Private room in Hopkinton
4.98 out of 5 average rating, 91 reviewsCozy 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 reviewsTranquil 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 reviewsUnique 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 reviewsWhite 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 reviewsThe 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 reviewsWindy 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 reviewsCozy, 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 reviewsJust 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 reviewsWhite 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 reviewsHistoric 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 reviewsCharming 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 reviewsCute 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.
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- Hampton Beach
- Boston Common
- TD Garden
- Fenway Park
- Harvard University
- North Hampton Beach
- Brown University
- New England Aquarium
- Monadnock State Park
- Faneuil Hall Marketplace
- Freedom Trail
- Prudential Center
- Symphony Hall
- Roger Williams Park Zoo
- Boston Public Library
- Crane Beach
- Rye North Beach
- Aaronap Cellars
- John Hancock Tower
- Boston Children's Museum
- Quincy Market
- USS Constitution Museum
- Pavilion Beach
- Water Park of New England
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