
Cottage holiday rentals in Boston
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Top-rated cottage rentals in Boston
Guests agree: These cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Boston cottage rentals
Cottage rentals with a hot tub

Waterfront Cottage in Summer Village w/ Grill
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.

Just Chill'inn Cottage
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!

Beach & pond cottage ! Westford MA and Boston!
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.

Lake Access & Pools: Sun-Soaked Westford Cottage!

Inviting Summer Village Cottage: Golf Cart & More!
Pet-friendly cottage rentals

Clean Waterfront Classic Cottage w/ Private Beach
I cannot say enough about what an amazing week we had at this adorable cottage. The views were stunning. The neighborhood was gorgeous. Check in was easy. The hosts were attentive made sure we had everything we needed and were very kind. 1000% would recommend and we hope to come back one day.

Tranquil Waterfront Retreat
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.

Retreat in the Trees- walk to Cape Hedge Beach
This place truly gave "treehouse" vibes - with being up on a hill and with the big windows, it was a pleasure waking up here each morning to see all the trees with their autumn leaves. This is such a unique house - and it included all the amenities we needed. The location was also great and it was easy to get around and explore the area. 10/10 would stay here again!

Beechwood Cottage
This was a great and quiet spot! It was easy to navigate to plus was close to town when we went exploring. The hosts are ridge across the driveway and came out one of the afternoons to say hello. They are super friendly and made the stay feel cozy! I’d come back to stay here again.

Sunny Airy Modern Oceanfront Cottage w/ Deck Wi-Fi
Great place to stay in Scituate right in town and within walking distance to the beach and restaurants/shops. Great communication with management. Would highly recommend !

NEW -Lakefront 2 Bed / 3 bath + Extra Bed
Hosts were very kind and responsive. The house was amazing and the views were incredible.

In-town 2 bedroom beach cottage with a pool
We were lucky enough to have a very extended stay at this lovely little bungalow! The house is so sweet! The layout is easy, the rooms are comfortably furnished, and the floors are beautiful, and there is an incredible library of books. The house is full of natural light, and nestled in a little private spot. There is lovely landscaping in the front yard, and the back yard is magical. The pool is amazing, and you feel like you are in your own little peaceful world here. The house is an easy walk to all of the things that make Rockport such a cool town. And, you can hear the ocean at night from the yard! Trent and Cassie are the best hosts! Kind, responsive, and mellow. We loved everything about our stay! We will be back. ( :

Carolyn's Cottage by the Sea
Carolyn’s Cottage is a lovely home. It is just as described and just 2 houses away from a very private beach. Having 2 outside tables is great, as we had 8 staying in the house and local family visiting for a few dinners. The neighborhood is quiet and the neighbors we met were friendly.
Private cottage rentals

The Little House - a historic New England cottage.
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.

Marblehead, Cottage on Whittier, new construction
Gorgeous cottage in a beautiful neighborhood. Perfect for celebrating our anniversary. Highly recommend the intimate setting.

Quaint & Cozy Gem ~ Walk to Sea ~ BBQ & Parking!
Superb cozy cottage in an ideal location. Very clean and exactly as advertised. Will book again without hesitation.

Bearskin Neck oceanfront w/ 2 parking spots!
It's a beautiful and cosy little house right next to a touristic street with restaurants and shops.

Quaint Oceanfront Cottage in Rockport MA
Great little place for two! Sandy the neighbor was great along with her dog! 😊 great walking distance to shopping and restaurants! View is beautiful and breathtaking 😎will be back again in two years! Cindy and Gary from Ontario

"Shore Bet" Humarock Beach Cottage - Scituate
We loved staying at "Shore Bet". It was in a great spot on the south part of Humarock. Beach entry close by. Front and rear decks for outside enjoyment. The grill was in great shape, and grilling on the back deck during sunset was magical. Everything was fantastic. The only things I'd comment on that weren't absolutely perfect, are nit-picky at best. I am a cook, so I'd have liked a few more knives, and another cutting board. See...NIT-PICKY! LOL. Truly a great place to stay that I'd recomment to anyone and everyone. Should we return to the area and "Shore Bet", or another of Jeff's properties are available, we will DEFINITELY stay there again. Thanks for a great place for our getaway, Jeff!

Cute Downtown Andover Cottage w/ Parking and Yard
We had a wonderful stay. Everything was exactly as described. The space was clean, quiet, and had everything we needed. We appreciated all of the supplies in the bathroom , kitchen, and laundry. Very easy to get into Boston, and surrounding towns. The patio space was peaceful and we enjoyed seeing all the birds and bunnies. This is a great location for visiting Merrimack. We had an easy time navigating to graduation. Thank you for a fabulous stay!

Deluxe oceanfront home sleeps 4 open concept
Beautiful, perfectly located house!! Cindy was so responsive and helpful. The instructions in the house were so helpful and there was everything we could have needed. Can’t say enough good things!
Quick stats about cottage rentals in Boston
Total rentals
10 properties
Nightly prices starting at
$66 NZD before taxes and fees
Total number of reviews
860 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
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