
Gloucester Schooner Adventure Hotels
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9 Oct - 11 Oct Top Schooner Adventure Hotel Reviews
The Vista
10/10 Excellent
"Rooms were clean. Pleasant stay. Staff was friendly and helpful."
Newly Renovated Luxury 5BR Home + Office, Walk to Beach & Town
10/10 Excellent
"Beautiful area! Walking distance to some great restaurants. Beautiful home!"
Single Level Home - Steps to Downtown Gloucester & A/C throughout
10/10 Excellent
"We loved our stay at Jo Ann's beautiful home! It was ideally located. -- walkable to shopping, restaurants, and major attractions -- and felt like our home away from home! Should you be visiting Gloucester, I would highly recommend her home. Amazing hospitality!"
WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC
10/10 Excellent
"Our visit to 21 Friend was outstanding as usual. We are repeat customers for this location for numerous reasons. The first reason is the hostess. Kathy is a true professional in what she provides as a hostess to every guest. She is easy to contact and willing to assist you in any way possible, The next positive factor is the amenties 21 Friend provides. I have rented Vrbo units worldwide and I have never seen a location exceeds the features/supplies and household items offered in 21 Friend street. As an example where have you found a grand piano in a rental unit - one is here. The kitchen is fully equipped with the basic essentials and Kathy has added bonus items such as a trash compacture, two ovens, and a cord of fire wood for the fireplace. Additionally, if you need something, just ask Kathy and she will probably find it somewhere in the house. Another important factor for choosing this location is the excellent cleaning aspects of 21 Friend st. After the cleaning service completes their work, Kathy followups with love and attention to every detail. Finally, the view from 21 Friend of the Gloucester Harbor is beautiful and every attraction the city has to offer is within a 10 minute drive. This is a great location to visit and my family and I look forward to every visit. p.s. we are already booked for 2027. Thanks Kathy"
Stay at East Gloucester
10/10 Excellent
"Great spot for a girls beach weekend!"
Cripple Cove Apartment in historic home across from harbour in Gloucester, MA
8/10 Good
"It was as expected based on the description and photos. Parking was easy. Linda was helpful and friendly while respecting our privacy. The place was older and funky, but clean and it is obviously cared about. The bed is a little saggy. Lots of stairs, not a problem for us or our dog but might be for some."
Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck
10/10 Excellent
"The place was perfect - clean, well-equipped, charming and exactly as described. Linda as host was also wonderful! We’ve visited Gloucester for decades and this was one of the best rentals we’ve ever had. Hats off to Linda and Hank. We had the best week and look forward to returning!"
Loft Townhouse in Downtown Gloucester #3
10/10 Excellent
"This was the perfect spot when in town for a wedding. The host was incredibly responsive and helpful throughout our whole stay. We were able to walk to local restaurants without worrying about driving. The rental was clean and perfect for our groups needs!"
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
10/10 Excellent
"This spot was perfect in so many ways! The unit had everything you’d need or want for cooking and most of all relaxing. The harbor view porch was definitely enjoyed by all. Very close to everything you love about Cape Ann."
Other attractions near Schooner Adventure

Cape Ann Museum
9.0/10 (23 reviews)
You can spend an afternoon exploring the galleries in Cape Ann Museum in Gloucester. Wander through the beautiful beaches and seaside in this family-friendly area.

Maritime Gloucester
9.4/10 (63 reviews)
You can spend an afternoon studying the exhibits at Maritime Gloucester during your trip to Gloucester. Wander through the beautiful beaches and seaside in this family-friendly area.

Pavilion Beach
8.0/10 (9 reviews)
Why not spend a lazy afternoon at Pavilion Beach during your trip to Gloucester?
Capt Bill & Sons Whale Watch
8.2/10 (12 reviews)
You can learn about the history of Gloucester with a stop at Capt Bill & Sons Whale Watch. Wander the seaside and beautiful beaches in the area.
Cape Ann Historical Museum
6.0/10 (1 review)
You can spend an afternoon browsing the exhibits at Cape Ann Historical Museum during your trip to Gloucester. Wander the seaside and beautiful beaches in the area.
Sargent House Museum
6.0/10 (1 review)
You can spend time exploring the galleries in Sargent House Museum during your travels in Gloucester. Wander the seaside and beautiful beaches in the area.
Gloucester Unitarian Universalist Church
After visiting Gloucester Unitarian Universalist Church, make a plan to see the other sights and activities in Gloucester.
Rocky Neck Art Colony
8.2/10 (20 reviews)
Take the family on an outing to Rocky Neck Art Colony during your trip to Gloucester. Wander the beautiful beaches and seaside in the area.