Cottage holiday rentals in Middlesex County

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Popular amenities for cottage rentals in Middlesex County

Cottage rentals with a hot tub

Cottage in Westford

Waterfront Cottage in Summer Village w/ Grill

ChrisRating, 5 stars10 months ago
If I could give this place 10 stars I would. We were traveling for work in Massachusetts and typically we stay at Marriott property. I checked Airbnb to find a place that was kid friendly and this popped up. It was a new listing with no reviews yet, and it ended up exceeding our expectations. This cute little cabin is right on the water. Although it is smaller for me, pure square footage perspective it’s a two bedroom one full bath with a loft that sleeps two kids so the way it was set up felt like plenty of space for us. It has kayaks and paddle boards. There’s a beach and there’s a community pool. There’s an exercise facility. It easily slept my wife and I plus two kids in a fun loft that they got to climb in and out of, and grandma that came to help us watch the kids. The staff at the resort were very friendly and easy to work with. It felt very safe and private. The AC worked well. The beds were very comfortable. Overall this is gem and we will be staying here again for sure.
Cottage in Westford
5 out of 5 average rating, 4 reviews

Just Chill'inn Cottage

JJRating, 5 stars9 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 favourite
Cottage in Westford
4.92 out of 5 average rating, 39 reviews

Beach & pond cottage ! Westford MA and Boston!

KatherineRating, 5 stars3 weeks ago
We needed a nice little place to stay while we visited family and friends. This was perfect. Cute and convenient, plus lots of fun amenities like a clubhouse, ball courts, kayaks and the lake. We went off season, so the pool was closed and it was too cold to boat, but it was still fun. We enjoyed walking the community, playing ping-pong and driving the golf cart.
Cottage in Westford
New place to stay

Lake Access & Pools: Sun-Soaked Westford Cottage!

Cottage in Westford

Inviting Summer Village Cottage: Golf Cart & More!

Private cottage rentals

Top guest favourite
Cottage in Winchester
4.96 out of 5 average rating, 71 reviews

The Little House - a historic New England cottage.

NancyRating, 5 stars1 week ago
our favorite “home” away from home thoughtful details abound, but nothing can compete with the beauty of the setting can highly recommend the spa pedicure at Winchester Nails
Top guest favourite
Cottage in Millis
4.99 out of 5 average rating, 129 reviews

Windy Knob Farm Cottage - stay on a working farm

NicoleRating, 5 stars1 week ago
We loved it here! The kids had so much fun watching the animals, and the grounds were secure and private. We would definitely stay here again!
Cottage in Concord
4.65 out of 5 average rating, 54 reviews

Tranquil Waterfront Retreat

AmandaRating, 5 stars3 weeks ago
We stayed here during our sisters law school graduation in Boston. It was the perfect location for us as we are outdoorsy and have our dog! My husband enjoyed the pond, did some fishing and we went out on the pond in the canoe! Beautiful area, walkable for the dog. We spent several mornings walking around the neighborhood. Short drive to Boston and it was away from the city traffic. The stairs were a lot, but we are young and in shape so we had no issues with it. Just be careful at night. The cottage had a keurig and small coffee pot which was perfect for us. No TV but it’s so peaceful, we read books and enjoyed the sounds of the water and the birds. Would stay again if we were in the area.
Superhost
Cottage in Groton
4.92 out of 5 average rating, 49 reviews

Cozy, 2BR lake-side retreat and outdoor oasis

AdamRating, 5 stars5 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 stars9 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 favourite
Cottage in Stow
4.96 out of 5 average rating, 180 reviews

White Pine Cottage

LisaRating, 5 stars4 days ago
Beautiful home on a lovely property. We felt right at home and wish we could have stayed longer. It was an incredible space and we look forward to returning.
Guest favourite
Cottage in Arlington
4.94 out of 5 average rating, 159 reviews

Historic 1880 Carriage House

ErikRating, 5 stars2 days ago
Excellent visit to this refitted barn which is now a multi-level home. Our stay was made even better by the hosts. Scott and Heather live on site and were always available for travel advice and local recommendations. Kids loved the backyard swing. The bus stop is at the end of the block and connects directly to the 'T' making public transit easy. Several restaurants are walking distance in downtown Arlington.
Top guest favourite
Cottage in Arlington
5 out of 5 average rating, 43 reviews

Charming Waterfront Cottage Near Cambridge/Boston

EricRating, 5 stars2 weeks ago
Sabrina's place was beautiful inside and out. The practically 180 degree view of Spy Pond is stunning and we enjoyed watching all of the natural beauty in this perfect little cottage. The space was spotless and thoughtfully decorated with just enough decor to give tons of character but still feeling uncluttered.

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