
Vacation rentals with a kayak in Gloucester
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Top-rated kayak rentals in Gloucester
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House rentals with a kayak

Northridge View
my friend and I from Tennessee were looking for a place to relax for a few days in New England. Ipswich was a delightful location, but we found it hard to leave the lovely view from the upper level of the home!

Waterfront House on Plum Island with Great View
We had a great mini-vacation at Mary Lou's airbnb! Everything was comfortable. The beach was so close and we could also walk to breakfast and lunch. Nice not to have to drive everywhere. If we get the opportunity we will definitely stay here again. Offered early check in when available and even late check out! We couldn't take advantage of that but so nice of her to offer! Great place!

Beach House on a Private Beach!
Oh my goodness. This place was a DREAM. Such a beautiful home with a view you can’t top. My husband and I stayed with our children and two friends for an east coast summer getaway and we could not have found a better place. Awesome setup, view, and Gaby could not have been more helpful. We would love to stay here again.

Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets
Had a great stay in Gloucester with a large group of friends and families from college. The house is as described with plenty of living and sleeping space for large groups. The screened porch is perfect for hanging out and eating in. The backyard is right on the water with plenty of outdoor games, a grill, fire pit, and paddle boards and a kayak to get on the water. Extremely family friendly with fun board games, life vests of all sizes, beach toys and floats etc. Location is great too, close to beaches, grocery stores and downtown Gloucester. Was the perfect space for a long weekend, and located very conveniently to Boston to accommodate families flying in from far away.

Dotey Cottage
I stay in quite a few Airbnb’s all over the world and this place does it right. The unexpected extras like things you always need in the kitchen when you arrive to an Airbnb to shampoo and conditioner in the shower to laundry detergent and dryer sheets.All there waiting for you. I grew up in Marblehead and this is a perfect location to be able to walk to beautiful Devereaux beach or around Marblehead neck. Backyard is a huge perk for this location as it is not common to have a backyard like this in an Airbnb this close to the beach. It isn’t huge it is exactly as described and was perfect for me and my two kids. Grill was great, there is a mini back deck, lots of games to play comfortable kitchen. Props to the owners you have done an awesome job and I will be recommending this Airbnb to my family and friends

2 bedroom waterfront retreat all seasons
The pictures don’t do this place justice! It’s so much more spacious than I was expecting and the decor was beautiful. We loved being on the lake and the area is so quiet and peaceful. The hosts were so responsive and proactive — they even installed brand new window AC units in the bedrooms without us asking because it was supposed to be in the 90s and they wanted to make sure the mini split didn’t leave us feeling too hot. The unit had everything we needed and the place was so comfortable. We honestly didn’t want to leave. We will definitely stay again!!!

Beachfront Home/Scenic walk to Harbor Eats & Shops
terrific place and location. the house is very well equipped with all the little things you might need, well maintained, all with very good taste and the owner is super responsive. we left two small items behind but mistake and the owner kindly sent us those the next day. 💯

Revere Beach House, Logan Airport, Bay Views
Our stay was great at Revere Beach. The house was exactly as described and the pictures were accurate. Alexander was FANTASTIC. He must work all the time because he responded immediately to every question we had. I wish he worked for me. Thanks for a great house and a great stay.
Cottage rentals with a kayak

*Oceanfront*AC* Families & Pets welcome* Renovated
Beautiful home! My family felt right at home. Kitchen had everything we needed and had toys and games for all ages. Antionette was very responsive to any questions and wrote back right away. Location was ideal. Easy walk to town and nearby lighthouse. Would recommend. Thank you for helping make a memorable vacation for my family.

Tranquil Waterfront Retreat
What a wonderful house. The location by the lake makes it truly special. I would love to come back again and again.

Cozy, 2BR lake-side retreat and outdoor oasis
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 with stunning ocean view and private beach
Lovely location and beautifully renovated home. Kitchen well appointed. Beds comfortable. Host very responsive. Would return.

Waterfront LakeHouse on Cobbetts!
Absolutely loved our stay at the lake house! The views were breathtaking, and the serene atmosphere made it the perfect getaway. The house was beautifully furnished and had all the amenities we needed. We enjoyed a cozy evening by the fire pit and loved fishing off the dock! The host was incredibly welcoming. Can't wait to come back! Highly recommend for anyone looking to relax and unwind.

Expansive coastal views, 3/2 newly renovated
We had high expectations — but the reality of this extraordinary spot exceeded them on all fronts. So tastefully and carefully decorated, everything new and spotless. The kitchen fully outfitted with brand new equipment and appliances, the most comfortable beds we’ve ever slept in in any Airbnb or luxury hotel (and great linens and pillows), wonderful flow from room to room, new, beautifully designed and perfectly functioning baths and windows/blinds, stylish and comfortable seating on the deck (and indoors), with more brand new seating flowing out onto the lawn. But what topped all that design perfection was the site’s natural beauty. Such privacy out on the point and because the view is almost 360, and primary orientation is toward sunset, the view all around are deep and exquisite, flowing out over marshland, tidal rivers to the bay. That made for fun paddle boarding, and even a brisk swim! For nature lovers, the bird life was so rich and varied. Heaven on earth

Relaxing Beachfront Cottage, 20min Ferry to Boston
This house was in a great location. It was very peaceful. The neighbors were friendly. The area was very nice and the people were nice. Would highly recommend.

Cottage on the Water
A wonderful retreat, just the perfect blend of charm and character. Easy and straightforward communication. Would definitely stay here again.
Cabin rentals with a kayak

Cabin Fever
We loved staying at Nicole's cabin and found it just as advertised. It is located on a pond so very peaceful to just hang out and enjoy. Several casual restaurants near by.

Big Fish, Little Lake - Fire Pit & Pvt Beach
We had such an amazing experience and everything was spectacular, definitely plan on going back!…thanks so very much!…

Little Lake, Big Fish - Fire Pit & Pvt Beach
Part 2 of my extended stay at this little cabin and the feeling remains the same. Great spot, private beach, comfortable bed, awesome fire pit. I thoroughly enjoyed my stay here, very peaceful and surrounded by nature. Definitely hope to return soon!

Modern Rustic Elegance on a Lake - Perfect Escape
Had a wonderful stay . Very relaxing and enjoyable cabin

Secluded Rustic Lakeside Cabin - Perfect Escape
Great spot, fantastic hosts, thank you!
Quick stats about vacation rentals with a kayak in Gloucester
Total rentals
10 properties
Nightly prices starting at
G$23,026 GYD before taxes and fees
Total number of reviews
660 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
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- Hampton Beach
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