
Vacation rentals with a kayak in Middlesex County
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Top-rated kayak rentals in Middlesex County
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Vacation rentals for every style
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Popular amenities for Middlesex County kayak rentals
House rentals with a kayak
Guest favorite

Home in Ashburnham
5 out of 5 average rating, 13 reviewsThe Nutty Bird Lakehouse
FinleyRating, 5 stars1 month ago
Such a beautiful spot! Kathy was extremely communicative - everything went smoothly and I did not need anything but she made herself available if I did. The home was clean and had everything needed for a relaxing stay. I hope to be back soon!

Private room in Canton
4.87 out of 5 average rating, 31 reviewsBoston area - Lakefront home 4 Br, 5.5 Ba L1
RahulRating, 5 stars11 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 stars5 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 Arlington
5 out of 5 average rating, 7 reviewsBright and open modern farmhouse
TonyRating, 5 stars8 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.

Home in Sutton
4.83 out of 5 average rating, 6 reviewsLake front home on Lake Singletary
CourtneyRating, 5 stars3 months ago
Adorable house on the lake. Clean and cozy. We all loved our stay. Thank you!
Superhost

Home in Shrewsbury
4.76 out of 5 average rating, 17 reviewsLake House near Boston 1
RachelRating, 5 stars2 weeks ago
Very pretty lakehouse in a great location! The amenities were incredibly nice and the hosts were super responsive, making for a great stay overall. The property is wonderful.
Guest favorite

Home in Westminster
4.9 out of 5 average rating, 181 reviewsLakefront, view of ski mtn, fireplace, sauna
EdwardRating, 5 stars1 week ago
Really liked the ocation right on the water and great size for us (two adults and 2 kids under 10). It was a quick trip and didnt spend as much time in Tyler's place as we wanted (since we were diving around a bunch visiting family and friends). But would certainly stay again next time we visit the area.

Home in Wakefield
5 out of 5 average rating, 3 reviewsEntire 1st Fl Condo, Lakeside, 5min walk to town
MaryRating, 5 stars16 months ago
Betsy’s home was wonderful. I had the whole first floor home with private entries and porches. The home is beautiful, it has quality finishes and furnishings. Loved the kitchen, bathroom and the bedroom has a very comfortable bed. Betsy even had the home decorated with a Xmas tree and candles, there was coffee, spices and more in the kitchen. It’s a great place and I plan on returning when I come to the Boston area. It’s an easy walk to the commuter rail that takes you to the North Station. I really appreciate Betsy’s hospitality. Thanks so much. Mary
Cottage rentals with a kayak
Top guest favorite

Private room in Hopkinton
4.98 out of 5 average rating, 91 reviewsCozy cottage in a quiet, lake community
HeatherRating, 5 stars2 weeks ago
I stayed with Nancy to start a new job for a month. Nancy was so helpful and caring. It was so nice to come back 'home' and walk in the woods or to the beach - what a sweet neighborhood. You do have to deal with some quirky things - like the aggressive neighborhood turkeys - but if you care about the environment (reduce/recycle) and enjoy walking/hiking/water sports, this place is for you.
Superhost

Cottage in Groton
4.92 out of 5 average rating, 49 reviewsCozy, 2BR lake-side retreat and outdoor oasis
AdamRating, 5 stars4 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 Concord
4.64 out of 5 average rating, 47 reviewsTranquil Waterfront Retreat
LucyRating, 5 stars2 weeks ago
Tranquil spot in a beautiful surrounding area. The views were incredible - the sunset was idyllic! The communication with the host was very clear and helpful as well. Thank you again

Cottage in Westford
5 out of 5 average rating, 4 reviewsJust Chill'inn Cottage
JJRating, 5 stars8 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, 36 reviewsBeach & pond cottage ! Westford MA and Boston!
MelanieRating, 5 stars6 months ago
We had an absolute blast on our girls getaway weekend!! The cottage and community were amazing, exactly what we were hoping for and Doug couldn't have been nicer or more helpful. He was always available by text or phone. The cottage was clean, nicely equipped, and a great location!! We will definitely be renting this cottage again on our next trip!!! Thanks for having us... we loved every minute!! 🧙🧙🧙
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- Hampton Beach
- Boston Common
- TD Garden
- Fenway Park
- Harvard University
- North Hampton Beach
- Brown University
- New England Aquarium
- Monadnock State Park
- Faneuil Hall Marketplace
- Freedom Trail
- Prudential Center
- Symphony Hall
- Roger Williams Park Zoo
- Boston Public Library
- Crane Beach
- Rye North Beach
- Aaronap Cellars
- John Hancock Tower
- Boston Children's Museum
- Quincy Market
- USS Constitution Museum
- Pavilion Beach
- Water Park of New England
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