Gloucester Wingaersheek Beach Hotels: 2026 Limited-Time Hotel Deals @Expedia

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Our top choices for Wingaersheek Beach hotels

A coastal scene with a sandy beach, rocky outcrops, and a lighthouse in the distance.

1. The Wylie Inn and Conference Center at Endicott College

17.2 km from Wingaersheek Beach

Berna

HK$923 total

includes taxes & fees

29 Nov - 30 Nov

A large hotel with multiple floors and a beach view.

2. Beauport Hotel Gloucester

Downtown Gloucester, 4.9 km from Wingaersheek Beach

Quevia

HK$1,866 total

includes taxes & fees

17 Nov - 18 Nov

A sunlit room with wicker furniture, large windows, and a view of greenery outside.

3. The Cove at Rockport Hotel

5.2 km from Wingaersheek Beach

Wendy

HK$1,087 total

includes taxes & fees

24 Nov - 25 Nov

A beach view from a balcony with a glass railing.

4. Blue - Inn on The Beach

18.7 km from Wingaersheek Beach

Andree

HK$1,687 total

includes taxes & fees

22 Nov - 23 Nov

A modern house with a large patio area featuring outdoor furniture and a fire pit.

5. Rockport Inn And Suites

4.8 km from Wingaersheek Beach

francisco

HK$1,175 total

includes taxes & fees

16 Nov - 17 Nov

A residential house with a stone pathway leading to the front door, surrounded by lush greenery and flowering plants.

6. Addison Choate Inn

5.2 km from Wingaersheek Beach

Don

HK$1,441 total

includes taxes & fees

23 Nov - 24 Nov

A large, two-story house with a prominent front porch, surrounded by well-maintained lawns and trees.

7. The Rockport House

5.7 km from Wingaersheek Beach

Ann

HK$1,501 total

includes taxes & fees

16 Nov - 17 Nov

A large, white, two-story building with a cylindrical tower, surrounded by well-maintained gardens and outdoor seating.

8. Briar Barn Inn

17.5 km from Wingaersheek Beach

Cleve

HK$1,745 total

includes taxes & fees

1 Dec - 2 Dec

A four-poster bed with a canopy, a zebra-patterned rug, and a view of the city through the window.

9. The Highliner Hotel

Downtown Gloucester, 4.6 km from Wingaersheek Beach

Matthew

HK$1,639 total

includes taxes & fees

16 Nov - 17 Nov

A modern living room with a green sofa, a leather couch, and a round coffee table. There are framed pictures on the wall and a chessboard on a small table.

10. The Ipswich Inn

12.8 km from Wingaersheek Beach

Sean

HK$968 total

includes taxes & fees

23 Nov - 24 Nov

A two-story building with a sign reading 'Harborview Inn.' There are two umbrellas in front of the building, and a rope barrier with flowers.

11. Harborview Inn

Downtown Gloucester, 4.7 km from Wingaersheek Beach

Martin

HK$1,656 total

includes taxes & fees

16 Nov - 17 Nov

A two-story house with a central entrance, multiple windows, and a well-maintained front yard.

12. Sally Webster Inn

5.9 km from Wingaersheek Beach

Laurel

HK$1,601 total

includes taxes & fees

16 Nov - 17 Nov

A covered porch with stone walls, wicker furniture, and a view of a house in the background.

13. Castle Manor Inn

4.1 km from Wingaersheek Beach

Corrine

HK$1,683 total

includes taxes & fees

16 Nov - 17 Nov

A coastal beach scene with a large house on a rocky outcrop, a sandy beach with people, and a clear blue sky.

14. The Vista

East Gloucester, 5 km from Wingaersheek Beach

Lisa

HK$1,693 total

includes taxes & fees

28 Nov - 29 Nov

A brick building with a sign reading "The Cabot Lodge."

15. The Cabot Lodge

19.4 km from Wingaersheek Beach

Karla

HK$1,530 total

includes taxes & fees

16 Nov - 17 Nov

A two-story house with a porch, a sign reading "THE BEVERLY," and a brick foundation.

16. The Beverly

18 km from Wingaersheek Beach

Amanda

HK$774 total

includes taxes & fees

1 Dec - 2 Dec

A restaurant with large windows overlooking a marina.

17. The Hotel at Cape Ann Marina

4.3 km from Wingaersheek Beach

Myles

HK$1,884 total

includes taxes & fees

16 Nov - 17 Nov

A couple walking on a sandy beach with buildings in the background.

18. Inn at Good Harbor Beach

East Gloucester, 5.6 km from Wingaersheek Beach

HK$2,750 total

includes taxes & fees

16 Nov - 17 Nov

View all properties

Compare popular hotels close to Wingaersheek Beach

Property	Property class	Guest rating
The Wylie Inn and Conference Center at Endicott College	3.5 star property	9.2 Wonderful 1,256 reviews	View
Beauport Hotel Gloucester	3.5 star property	9.6 Exceptional 1,002 reviews	View
The Cove at Rockport Hotel	2.5 star property	9.0 Wonderful 214 reviews	View
Blue - Inn on The Beach	3.5 star property	9.6 Exceptional 251 reviews	View
Rockport Inn And Suites	2.5 star property	8.6 Excellent 1,518 reviews	View

Hotels recommended for families near Wingaersheek Beach

Castle Manor Inn

Gloucester

HK$1,683 total

includes taxes & fees

16 Nov - 17 Nov

Top Wingaersheek Beach Hotel Reviews

Sunset Cove: Waterfront living on the Annisquam River

8/10 Good

"This is a beautiful property and the location is super- but be prepared for a little road noise. If you’re looking for quiet on the water, this isn’t it. Location wise, and views- absolutely beautiful. The home is well equipped and tastefully decorated. Overall I’d stay here again. The only issue we really had was that when we received all the check in information, at the bottom of the page it said “your access code is…” and there was no access code. We looked for it for 15 minutes but it simply wasn’t there. It was cold, windy and dark- really poor cell service. We called the host number and had to press 2 for emergencies. We were hung up on twice- and when she finally stayed on the line- she couldn’t find my reservation. She kept me on hold for 20 minutes looking for it. While I was waiting, I had my sister call the number to see if we could get someone else on the line- and he immediately found our reservation. She was abrupt and disinterested in helping me and it was disappointing. But after all of that- it was a nice, old coastal home with pretty views in a great little community. We went to a cute little restaurant for breakfast several times while we were there (George’s) and they were amazing. We loved our stay here."

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

10/10 Excellent

"This was the perfect house for a mini family vacation! We had so much room to spread out and plenty of hang out spots for everyone to be together! Multiple living rooms, good size kitchen and in a beautiful location! Walk to the gorgeous beach and tour the nearby homes, the location was fabulous! It is a good solid half hour or so to downtown Salem, we drove in daily. We were looking forward to an actual outdoor hottub as the listing describes but it is only a jacuzzi tub fyi. The decks, natural lighting and beautiful views were unmatched. We would stay here again!"

Gull's Nest - Ocean Views from the Living Room

10/10 Excellent

"The property was beautiful, perfect for our needs. We had a great time, enjoying the views, and the neighborhood! The house was comfortable, beds and living area! We had no need to contact the host. The reasons for minus one star,The downstairs area was a little musty, maybe because it was shoulder season and the house had been closed up? Second thing, no heat! We could have used a little to take the chill of early morning or before bed, I understand that some people may abuse the heat.Those small things did not take away from us having a wonderful time!"

Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive

10/10 Excellent

"My wife and I had a wonderful stay. The cottage is just as beautiful as the pictures would suggest and certainly very well-equipped. What we didn't realize when we booked this cottage was the uniqueness of the location. Our only criteria was to be on the water, but this was much more than that. Nearby there is a walking bridge to Annisquam which is filled with quaint narrow streets and beautiful homes. We could walk and paddle to beautiful beaches and watch the coming and goings of boats. The people were also very friendly and we were excited to see the first annual paddle of the "Witches of Annisquam."My wife and I highly recommend Riverdock Cottage."

Clean Waterfront Classic Cottage with Private Beach

10/10 Excellent

"We love Jean’s home! You cannot get closer to the water. We’ve stayed several times. The bathroom and kitchen are small, the bedrooms quirky yet very comfortable, and it’s not a spot for young kids or those with mobility challenges. That said, WE LOVE IT!! This home is stocked well enough to prepare any kind of a meal and you can’t beat the view during prep. You literally cannot go an hour without feeling completely relaxed with all that water view and the gentle lapping of the Annisquam river. Please don’t take my review to heart, because we want the home for our next Gloucester getaway…"

Evensong: Oceanview Retreat with Dock

10/10 Excellent

"This was an absolutely beautiful property in a great area. The house was clean and looked exactly as pictured. The view of the water was phenomenal! Katie was so easy to communicate with! The house is far enough away from all the crazy of Salem but was close enough for us to have an amazing day trip! Perfect for our girls trip and all 8 of us would recommend the property!"

Other attractions near Wingaersheek Beach

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.

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Frequently asked questions

What's the area like around Wingaersheek Beach?

Wingaersheek Beach is located in Gloucester. This historic area is known for its beautiful ocean views and whale watching. If you're looking for a convenient place to stay, take a look at the 26 hotels and other accommodation options you'll find within a mile.

What's the best hotel to stay close to Wingaersheek Beach?

Rockport Inn And Suites is one of the top choices for your stay based on our traveller data, and this B&B offers free breakfast and an indoor pool. It's located 3 mi (4.8 km) from Wingaersheek Beach.

How many hotels should I expect to find near Wingaersheek Beach?

Expedia has 26 hotels and other accommodation options within a mile from Wingaersheek Beach.

If I need to cancel the hotel reservation for my stay near Wingaersheek Beach, will I receive a refund?

Yes! You'll find that most hotel reservations are fully refundable if cancelled before the hotel's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of booking. Enter your dates, click on "Search", then use the filter option "fully refundable" to view the best deals available near Wingaersheek Beach.

What can I see and do near Wingaersheek Beach?

Cape Ann Museum, Maritime Gloucester and Hammond Castle feature a variety of fascinating exhibits to see while you're in town. Motif No 1, Dogtown and Paper House are notable landmarks to explore if you're in the area. You can enjoy live performances at Shalin Liu Performance Center and The Gorton Theatre.

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Gloucester Wingaersheek Beach Hotels

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Our top choices for Wingaersheek Beach hotels

1. The Wylie Inn and Conference Center at Endicott College

2. Beauport Hotel Gloucester

3. The Cove at Rockport Hotel

4. Blue - Inn on The Beach

5. Rockport Inn And Suites

6. Addison Choate Inn

7. The Rockport House

8. Briar Barn Inn

9. The Highliner Hotel

10. The Ipswich Inn

11. Harborview Inn

12. Sally Webster Inn

13. Castle Manor Inn

14. The Vista

15. The Cabot Lodge

16. The Beverly

17. The Hotel at Cape Ann Marina

18. Inn at Good Harbor Beach

Compare popular hotels close to Wingaersheek Beach

Hotels recommended for families near Wingaersheek Beach

Castle Manor Inn

Top Wingaersheek Beach Hotel Reviews

Sunset Cove: Waterfront living on the Annisquam River

Other attractions near Wingaersheek Beach

Cape Ann Museum

Frequently asked questions

Explore a world of travel with Expedia