
Cottage holiday 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

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.
Top Guest favourite

Cottage in Westford
5 out of 5 average rating, 5 reviewsJust Chill'inn Cottage
JJRating, 5 stars10 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!
Superhost

Cottage in Westford
4.92 out of 5 average rating, 39 reviewsBeach & pond cottage ! Westford MA and Boston!
KatherineRating, 5 stars1 month 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 stayLake 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, 72 reviewsThe Little House - a historic New England cottage.
TracyRating, 5 starstoday
This is a lovely home in a perfect location. Taking morning coffee on the screened-in porch overlooking the pond was easily the best part of our days. We very much hope to return soon.
Top Guest favourite

Cottage in Millis
4.99 out of 5 average rating, 129 reviewsWindy Knob Farm Cottage - stay on a working farm
NicoleRating, 5 stars2 weeks 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, 55 reviewsTranquil Waterfront Retreat
TanyaRating, 5 stars2 weeks ago
Enjoyed our stay at this lake house. Beautiful surroundings, wish we had more time on our trips to use the kayaks to explore the lake. We would stay again.
Superhost

Cottage in Groton
4.92 out of 5 average rating, 49 reviewsCozy, 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.
Top Guest favourite

Cottage in Westford
5 out of 5 average rating, 5 reviewsJust Chill'inn Cottage
JJRating, 5 stars10 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 reviewsWhite Pine Cottage
LisaRating, 5 stars1 week 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, 160 reviewsHistoric 1880 Carriage House
ErikRating, 5 stars1 week 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, 44 reviewsCharming Waterfront Cottage Near Cambridge/Boston
WinterRating, 5 stars3 days ago
We had an amazing & relaxing few days here! Close to everything and being right on the water is so peaceful. The house was spotless, bathroom was clean & the shower was warm! We would absolutely stay here again.
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- Boston Common
- Fenway Park
- Revere Beach
- TD Garden
- Harvard University
- Lynn Beach
- Brown University
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- North Hampton Beach
- New England Aquarium
- Monadnock State Park
- Faneuil Hall Marketplace
- Freedom Trail
- Crane Beach
- Canobie Lake Park
- Good Harbor Beach
- Prudential Center
- Roger Williams Park Zoo
- MIT Museum
- Rye North Beach
- Museum of Fine Arts, Boston
- Quincy Market
- Bunker Hill Monument
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