Cottage holiday rentals in Middlesex County

Find and book unique cottages on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for cottage rentals in Middlesex County

Cottage rentals with a hot tub

Cottage in Westford
4.67 out of 5 average rating, 3 reviews

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 reviews

Just 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 reviews

Beach & 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 stay

Lake Access & Pools: Sun-Soaked Westford Cottage!

Cottage in Westford

Inviting Summer Village Cottage: Golf Cart & More!

Pet-friendly cottage rentals

Guest favourite
Cottage in Stow
4.96 out of 5 average rating, 181 reviews

White Pine Cottage

DianeRating, 5 stars4 days ago
Entering the cottage for the first time was like walking into a delightful and spotless Alice -in - Wonderland space. Despite the wooded setting, the cottage was light and bright. The room layout had nooks for privacy as well as larger spaces for socializing. The window seat in the living room was made for reading; a small parlor facing the front enabled private conversations. The dining table was perfect for our evening game of Uno. My niece immediately adopted the loft for her own space. Nearby Hudson provided a variety of restaurants and a river walk. We were only sad that we had but one day to spend here.
Cottage in Concord
4.66 out of 5 average rating, 58 reviews

Tranquil Waterfront Retreat

GeraldRating, 5 stars2 weeks ago
What a wonderful house. The location by the lake makes it truly special. I would love to come back again and again.
Top guest favourite
Cottage in Worcester
4.89 out of 5 average rating, 125 reviews

Unique and Private Cottage in Worcester

ElaineRating, 5 stars2 months 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.
Cottage in Littleton
New place to stay

Peaceful Cozy Adorable Cottage

Private cottage rentals

Top guest favourite
Cottage in Winchester
4.96 out of 5 average rating, 72 reviews

The Little House - a historic New England cottage.

TracyRating, 5 stars1 week ago
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 reviews

Windy Knob Farm Cottage - stay on a working farm

NicoleRating, 5 stars3 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
4.66 out of 5 average rating, 58 reviews

Tranquil Waterfront Retreat

GeraldRating, 5 stars2 weeks ago
What a wonderful house. The location by the lake makes it truly special. I would love to come back again and again.
Superhost
Cottage in Groton
4.92 out of 5 average rating, 49 reviews

Cozy, 2BR lake-side retreat and outdoor oasis

AdamRating, 5 stars6 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.
Guest favourite
Cottage in Stow
4.96 out of 5 average rating, 181 reviews

White Pine Cottage

DianeRating, 5 stars4 days ago
Entering the cottage for the first time was like walking into a delightful and spotless Alice -in - Wonderland space. Despite the wooded setting, the cottage was light and bright. The room layout had nooks for privacy as well as larger spaces for socializing. The window seat in the living room was made for reading; a small parlor facing the front enabled private conversations. The dining table was perfect for our evening game of Uno. My niece immediately adopted the loft for her own space. Nearby Hudson provided a variety of restaurants and a river walk. We were only sad that we had but one day to spend here.
Guest favourite
Cottage in Arlington
4.94 out of 5 average rating, 160 reviews

Historic 1880 Carriage House

ErikRating, 5 stars2 weeks 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 reviews

Charming Waterfront Cottage Near Cambridge/Boston

WinterRating, 5 stars1 week 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.
Top guest favourite
Cottage in Andover
4.91 out of 5 average rating, 44 reviews

Cute Downtown Andover Cottage w/ Parking and Yard

MichelleRating, 5 stars3 weeks ago
This is our second time staying at Rick and Christina’s gorgeous Andover home. As someone who grew up in the town, this location and the house itself feels nostalgic, cosy, and familiar. Whether you’re new to exploring north of Boston, or a returning hometown visitor, this location is a treasure. We will most certainly visit again and again. Thank you for having our little family visit once again!

Destinations to explore