
Holiday rentals with a kayak in Middlesex County
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Top-rated Accommodation with a Kayak in Middlesex County
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.
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Holiday House Rentals with a Kayak

Private room in Canton
4.87 out of 5 average rating, 31 reviewsBoston area - Lakefront home 4 Br, 5.5 Ba L1
RahulRating, 5 stars13 months ago
We had a great stay in this luxurious house by a lake. The view of the lake from many areas of the house (including many bedrooms and the dining area) is amazing. The house is very spacious (4 levels) with large bedrooms. Every bedroom has an attached bathroom which helped us a lot since we were a party of 9. The house is tastefully furnished and very well maintained. The kitchen is large and well equipped. The neighborhood is safe though a bit of a drive from main Boston areas like Cambridge (~30 minutes). This is a perfect place if you have many in your party and want to unwind in a super comfortable spacious house. The weather was not great so we could not spend time in the large well-kept backyard and explore the lake. The hosts live in the house but are barely noticeable. They are a friendly couple. Thank you Kevin and Jessie for hosting us!
Superhost

Private room in Milton
4.78 out of 5 average rating, 23 reviewsSerene Bright Private Bedroom in Deluxe Unit
DorotaRating, 5 stars7 months ago
I will recommend Jennifer’s place to everyone and I’ll be back next time when visiting Massachusetts. Thank you Jennifer for your hospitality 😊

Home in Sutton
4.83 out of 5 average rating, 6 reviewsLake front home on Lake Singletary
CourtneyRating, 5 stars5 months ago
Adorable house on the lake. Clean and cozy. We all loved our stay. Thank you!

Home in Arlington
5 out of 5 average rating, 7 reviewsBright and open modern farmhouse
TonyRating, 5 stars10 months ago
This place is a gem!! It sits in a super quiet neighborhood and close to Alewife metro station for trips into Boston. The house was perfect for our family of 6 (4 teenagers). The house was quaint, clean, and spacious enough for all us to feel like home for a few days. Aimee was super helpful in providing local recommendations for groceries and restaurants. She was also very proactive in checking in with us to see if we needed anything. Super host!! If you are traveling to Boston, this is a fantastic place to stay. Definitely would stay here again if we return at any point.
Superhost

Home in Shrewsbury
4.83 out of 5 average rating, 23 reviewsLake House near Boston 1
LaurenRating, 5 stars1 week ago
We had a group of four girlfriends coming to town for an anniversary party and the four of us stayed at Anne and Giovanni's place. It was easy to find, right off the main road, and check in was very easy. There are three real bedrooms with a queen each, the fourth bedroom is an attic/playroom with a bunk bed, so our fourth person elected to sleep on the fold out couch downstairs, which was very comfortable. There are two full bathrooms, one upstairs and one downstairs, which was plenty for our four adults. We had a full day of rain which turned out great b/c we sat in the screened in porch all day and caught up and watched the rain on the lake. We had everything we needed and the house was a lovely place to spend a long weekend together! Check out was very easy and our hosts were communicative throughout. We would stay there again!
Guest favourite

Home in Westminster
4.89 out of 5 average rating, 188 reviewsLakefront, view of ski mtn, fireplace, sauna
BenRating, 5 stars3 weeks ago
This spot was excellent for my group. There were plenty of comfortable sleeping options for everyone and the space was even more spacious than expected. We also enjoyed the views and peaceful surroundings of the pond. Tyler was able to accommodate a late checkout as well, which was greatly appreciated.

Home in Shrewsbury
4.71 out of 5 average rating, 7 reviewsPrivate Lake Cottage Retreat
StephaneRating, 5 stars4 months ago
Very cool location on lake Quinsigamond. My girlfriend and I spent the weekend ice fishing and relaxing. House was cozy and near good food and amenities. Tj was quick to respond and make sure all was well. Would definitely recommend if in the area.
Guest favourite

Home in Melrose
4.79 out of 5 average rating, 47 reviewsQuiet Entire house, Boston close, MBTA, com rail
CarrieRating, 5 stars1 week ago
Great little private house, with a private backyard. Had everything we needed, and then some. Very clean. Will stay again! Thanks, Adam!
Cottages with a kayak
Top Guest favourite

Private room in Hopkinton
4.98 out of 5 average rating, 94 reviewsCozy cottage in a quiet, lake community
KristanRating, 5 stars3 weeks ago
I really enjoyed my time here in Nancy’s welcoming and comfortable home. She’s super proactive so I was so well prepared even before I even arrived. Once there, I loved the super clean and serene space.

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!
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.
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- Hampton Beach
- Boston Common
- Fenway Park
- Revere Beach
- TD Garden
- Harvard University
- Lynn Beach
- Brown University
- Duxbury Beach
- 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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