The Best Hotels Closest to Wingaersheek Beach in Gloucester - 2026 Updated Prices

A rocky shoreline with large boulders and a distant view of houses and trees.

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Our top choices for Wingaersheek Beach hotels

Two individuals in white robes by a window overlooking a body of water with a distant shoreline.

A hotel room with a large bed, a fireplace, a television, and a view of the water.

A bar area with a long counter, multiple bar stools, and a variety of bottles and glasses.

A seafood display with shrimp and seaweed, a bar area with glasses and bottles, and a view of the city through large windows.

1. Beauport Hotel Gloucester

Downtown Gloucester, 3 mi from Wingaersheek Beach

Patricia

£158

includes taxes & fees

3 Nov - 4 Nov

A bar area with wooden ceiling beams, hanging pendant lights, and a bar stocked with various bottles. There are six wooden bar stools with cushioned seats.

A staircase with a sign reading "BAGGAGE ROOM" leading to a living area with a sofa and a lamp.

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

A spacious living room with a staircase, a sofa set, and a large window.

2. Briar Barn Inn

10.9 mi from Wingaersheek Beach

Cleve

£154

includes taxes & fees

2 Nov - 3 Nov

A wooden deck with outdoor seating, overlooking a body of water and a rocky shoreline.

An outdoor patio with wooden tables and chairs, a pergola, and a view of the water and hills.

A hotel room with two beds, a small table with a chair, a TV, and a view of the sea through the window.

A view from inside a room with large windows overlooking a street. There are potted plants on the windowsill and outside.

3. Bearskin Neck Motor Lodge

3.6 mi from Wingaersheek Beach

Mary Beth

£202

includes taxes & fees

1 Nov - 2 Nov

A large, white, two-story building with a balcony and a staircase leading to a lower level.

A poolside area with outdoor seating, a fire pit, and a building with multiple balconies and outdoor lighting.

A wooden boardwalk leading to a beach with a clear sky.

A rooftop pool area with lounge chairs and a view of the ocean.

4. Ocean House Hotel at Bass Rocks

East Gloucester, 4 mi from Wingaersheek Beach

Michelle

£142

includes taxes & fees

3 Nov - 4 Nov

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

A wooden-paneled room with a staircase, a chair, and a table.

A large, two-story house with a wrap-around porch and a stone foundation.

A corner room with two wicker chairs, a small wooden chest, and a window with a view of greenery.

5. Castle Manor Inn

2.6 mi from Wingaersheek Beach

Barb

£161

includes taxes & fees

22 Oct - 23 Oct

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

A harbor with boats docked near a red building with an American flag.

A house with a covered patio, a stone pathway, and a fenced backyard.

A spacious living room with exposed wooden beams, a fireplace, and modern lighting fixtures.

6. Rockport Inn And Suites

3 mi from Wingaersheek Beach

Marci

£113

includes taxes & fees

3 Nov - 4 Nov

A dining area with a view of the ocean, white chairs, a wooden table, and a vase with a plant.

A beach with a wooden fence, sandy shore, and ocean waves.

A beachfront property with a multi-story building, a balcony with glass railings, and several beach chairs arranged in front.

A bright, sunlit room with a dining area featuring wooden chairs and a table, a kitchen with white cabinets, and a large window offering a view of greenery outside.

7. Blue - Inn on The Beach

11.6 mi from Wingaersheek Beach

Victor

£219

includes taxes & fees

15 Nov - 16 Nov

An aerial view of a town with a prominent church, residential houses, and a large green arrow pointing downwards.

A balcony with a table set for two, featuring a bottle of wine and glasses. A chair with a towel draped over it is visible.

A dining area with a wooden table, chairs, and a ceiling fan.

A spacious living room with hardwood floors, a grey sofa, and a blue armchair. A kitchen with white cabinets and a refrigerator is visible in the background.

8. Eagle House Motel

3.3 mi from Wingaersheek Beach

Glen

£173

includes taxes & fees

1 Nov - 2 Nov

A restaurant with large windows overlooking a marina.

A marina with boats docked, outdoor seating with umbrellas, and a view of the water.

A spacious indoor area with large windows, a yellow sofa, patterned ottoman, and a blue coffee table.

A neatly made bed with a tray holding a bottle of Chandon champagne and two glasses, a large headboard, and a modern chandelier.

9. The Hotel at Cape Ann Marina

2.7 mi from Wingaersheek Beach

Myles

£181

includes taxes & fees

1 Nov - 2 Nov

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

A bar area with a flat-screen TV, bar stools, a counter with various bottles, and a coffee machine.

A gym with treadmills, elliptical machines, and weight equipment.

A dining area with striped tablecloths and wooden chairs, set outdoors with a building in the background.

10. The Wylie Inn and Conference Center at Endicott College

10.7 mi from Wingaersheek Beach

Berna

£89

includes taxes & fees

16 Nov - 17 Nov

A cozy living room with a leather sofa, a round coffee table with books and a disco ball, a fireplace, and a bookshelf.

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.

A cozy loft bedroom with a large window, wooden flooring, a green sofa, a dining table with chairs, and a TV on a stand.

A spacious kitchen with a wooden bar area, white cabinetry, and a large window offering a view of the outdoors.

11. The Ipswich Inn

8 mi from Wingaersheek Beach

Donna

£101

includes taxes & fees

4 Nov - 5 Nov

A modern hotel room with a large bed, a flat-screen TV, a fireplace, and a chandelier.

A modern living room with a sofa, a small table, a zebra-patterned rug, and a staircase.

A modern living room with a white sofa, a zebra-patterned rug, and a large framed picture on the wall.

A modern living room with a fireplace, a mounted TV, and a bar area with a bottle of champagne.

12. The Highliner Hotel

Downtown Gloucester, 2.9 mi from Wingaersheek Beach

Matthew

£250

includes taxes & fees

8 Nov - 9 Nov

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Compare popular hotels close to Wingaersheek Beach

Property	Property class	Guest rating
Beauport Hotel Gloucester	9.6 Exceptional 1,003 reviews	View
Briar Barn Inn	9.6 Exceptional 886 reviews	View
Harborview Inn	9.6 Exceptional 339 reviews	View
Bearskin Neck Motor Lodge	9.8 Exceptional 202 reviews	View
Ocean House Hotel at Bass Rocks	9.0 Wonderful 875 reviews	View

Top Wingaersheek Beach Hotel Reviews

Annisquam Singing Pines: Riverfront Splendor

10/10 Excellent

"Excellent house. Very clean, big enough to accommodate our extended family. Would definitely recommend to others."

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!"

Quirky 1-bedroom apartment with AC in delightful Gloucester, near water

10/10 Excellent

"Quirky was accurate, but in a most charming way. The outside of the building fooled us, but inside we were met with an attractive and wide-open spaced living area, a VERY comfortable and well appointed queen bed (SOOO important no matter how long the stay), ample towels, ample fridge space, ample cleanup provisions, ample supplies of coffee and tea, a user-friendly coffee maker, an unpretentious (and why not) restroom area, a space heater AND air conditioner if needed, a ROKU tv with which to connect to our favorite channels, and last but not least (unlike MANY Vrbo properties), the easiest and shortest departure todo list I’ve ever experienced.The host, Inge, was immediate with every communication, making us feel that she would be at the ready if anything untoward came upon us.Incidentally, we almost gave up searching in Gloucester when all we had initially uncovered were rentals with multi-day requirements and 4-digit costs. Inge’s property could not have come at a better time for us when needing to catch the art show just down the road a piece at the Queen Ann Museum.All tolled, the nor’easter was a mere blip on the radar for us the whole weekend, every bit for having the perfect hideaway at Inge’s place for my honey and I.Thank you muchly, Inge.Sincerely, Doc"

Sunset Cove: Waterfront living on the Annisquam River

8/10 Good

"We are from the north shore of Boston and we travel there every year to visit friends. Our pick to stay this year was Sunset Cove. Unfortunately there was a Nor’Easter, we didn’t get to enjoy any of the outdoor space which I’m sure is great with nice weather. The house was clean but the living room couch had a smell to it which became very unpleasant. The shower in the upstairs bedroom needs to be fixed as it leaks down the wall. The kitchen was very well stocked with dishes, glasses, cooking utensils etc. The next door neighbor knocked on the door to tell us that the basement, where the master bedroom is, floods terribly during storms. This did not happen but it was kind of a weird visit. Overall we had a great time visiting friends. Check-in and check-out was very easy. We had a slight glitch, not even worth mentioning but the host was very friendly and helpful and it was resolved quickly."

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

10/10 Excellent

"Lovely waterfront home, nicely furnished and decorated. We enjoyed the open concept first floor and deck. Bedrooms were spacious, beds very comfortable. All in all, would highly recommend."

Beautiful Oceanfront Home in Estate Setting Gloucester — FALL RENTAL AVAILABLE!

10/10 Excellent

"Beautiful house with great views of Ipswich Bay as well as nearby pond/wetland"

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

8/10 Good

"We had a lovely time at the beach. Beach chairs and towels provided. Loved that we could bring our small dog. We unfortunately only had AC in one back upstairs bedroom so there were a couple warm afternoons/evenings where the downstairs was 80 degrees. Overall a great week would return."

Clean Waterfront Classic Cottage with Private Beach

10/10 Excellent

"Great location to relax and enjoy! Second time staying and looking forward to coming back!"

Gull's Nest - Ocean Views from the Living Room

10/10 Excellent

"This property is as discribed, clean, nice view. One issue was trash didn’t get picked up on scheduled day and when I called the office they said it would be picked up the next morning but no one ever came. I do feel it was overpriced as we have rented in Gloucester for the past 6 years in 5 different homes. We only rented for 10 days this time instead of 2 weeks because of the price."

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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Coffins Beach

Why not spend a lazy afternoon at Coffins Beach during your trip to Gloucester? While you're in the area, stroll along the seaside.

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Dogtown

6.0/10 (1 review)

Find out about the history of Gloucester when you spend time at Dogtown. Wander the seaside and beautiful beaches in the area.

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Plum Cove Beach

8.0/10 (2 reviews)

If a restful holiday is part of your travel plans, Plum Cove Beach might be the perfect place to visit during your trip to Gloucester. While you're in the area, stroll along the seaside.

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Paper House

8.0/10 (29 reviews)

You can learn about the history of Rockport with a trip to Paper House. Wander the seaside and beautiful beaches in the area.

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Halibut Point Reservation

9.6/10 (14 reviews)

You can learn about the history of Rockport when you stop by Halibut Point Reservation. Wander the seaside and beautiful beaches in the area.

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Gloucester Unitarian Universalist Church

After visiting Gloucester Unitarian Universalist Church, make a plan to see the other sights and activities in Gloucester.

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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.

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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.

Search Hotels Near Wingaersheek Beach, Gloucester

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Wingaersheek Beach hotels

1. Beauport Hotel Gloucester

2. Briar Barn Inn

3. Bearskin Neck Motor Lodge

4. Ocean House Hotel at Bass Rocks

5. Castle Manor Inn

6. Rockport Inn And Suites

7. Blue - Inn on The Beach

8. Eagle House Motel

9. The Hotel at Cape Ann Marina

10. The Wylie Inn and Conference Center at Endicott College

11. The Ipswich Inn

12. The Highliner Hotel

Compare popular hotels close to Wingaersheek Beach

Top Wingaersheek Beach Hotel Reviews

Annisquam Singing Pines: Riverfront Splendor

Evensong: Oceanview Retreat with Dock

Quirky 1-bedroom apartment with AC in delightful Gloucester, near water

Sunset Cove: Waterfront living on the Annisquam River

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

Beautiful Oceanfront Home in Estate Setting Gloucester — FALL RENTAL AVAILABLE!

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Clean Waterfront Classic Cottage with Private Beach

Gull's Nest - Ocean Views from the Living Room

Other attractions near Wingaersheek Beach

Cape Ann Museum

Coffins Beach

Dogtown

Plum Cove Beach

Paper House

Halibut Point Reservation

Gloucester Unitarian Universalist Church

Sargent House Museum

Frequently asked questions