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

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Our top choices for Wingaersheek Beach hotels

1. Sally Webster Inn

5.9 km from Wingaersheek Beach

V. CHARLENE

HK$1,884 total

includes taxes & fees

12 Aug - 13 Aug

Iron/ironing board, free WiFi, bed sheets

2. The Rockport House

5.7 km from Wingaersheek Beach

Molly

HK$1,569 total

includes taxes & fees

29 Jul - 30 Jul

3. The Cove at Rockport Hotel

5.2 km from Wingaersheek Beach

Tara

HK$3,121 total

includes taxes & fees

9 Aug - 10 Aug

Laptop workspace, iron/ironing board, free WiFi

4. The Highliner Hotel

Downtown Gloucester, 4.6 km from Wingaersheek Beach

Matthew

HK$3,020 total

includes taxes & fees

19 Jul - 20 Jul

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Top Wingaersheek Beach Hotel Reviews

Rockport Inn And Suites

8/10 Good

"The room was good sized and clean, but the sheets need to be upgraded."

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

10/10 Excellent

"This is our second time staying at this house for our summer vacation. The location is wonderful - it is only a 5 minute walk to a beautiful, private beach. Our dogs enjoyed walking with us on the beach every morning and evening. The neighborhood was quiet and we saw deer and turkey in the yard. The house was very clean and had plenty of space. We appreciated the air conditioning on the warmer days. We were very close to our whale watching trips and to several restaurants. Jennifer was quick to respond to any communication and contacted us prior to arrival with our check in information. We hope to stay in this location for future vacations!"

Clean Waterfront Classic Cottage with Private Beach

10/10 Excellent

"Immaculate cute cottage with a fabulous ocean view. We enjoyed sitting on the porch watching the boats go by. They had paddle boards and a kayak that you can launch right from the private beach. I loved having the ocean breeze through the windows an hearing the lapping of the waves. Quiet, peaceful, perfect. The host was great at answering questions and very responsive. Great week long experience."

Oceanfront Dock Escape ~ Kayaks & Paddleboards

10/10 Excellent

"Very old home, nicely restored. Comfortable beds, very cute and fitting decor. The kitchen was disappointing- small won’t expect to cook for a larger family, the kitchen was dirty. I would not describe it as fully stocked. There are plates and some pots and pans and small appliances. The rest is odds and ends left from prior guests. The back patio overlooking the bay is very peaceful!!!"

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

10/10 Excellent

"This was the perfect house for our son’s college graduation celebration. Family and friends enjoyed eating lunch on the two decks, playing cornhole in the driveway, shooting pool in the large family room and walking to the beach. The house was fully stocked with everything we needed."

Evensong: Oceanview Retreat with Dock

10/10 Excellent

"This is a lovely property where our extended family shared a wonderful Father’s Day Weekend celebration. The home itself is comfortable, immaculately clean, and thoughtfully appointed. The location is ideal for exploring Gloucester and Rockport, within 10-15 minutes of all the major attractions in each. Most of all, the views from the home onto the water outside are truly majestic!! Truly extraordinary. Katie is an incredibly responsive and helpful host. I most highly recommend this property for your next visit to the North Shore!"

Waterfront Home with Spectacular Viewsof the Annisquam River

8/10 Good

"The view from this property was incredible, so relaxing. The house is very old and outdated, in need of some repairs and refresh, but it was enough to accommodate our group since we are close. It is definitely rustic, but had the essentials. "

Hotels near other Wingaersheek Beach attractions

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. Another good option is Castle Manor Inn, located 2.6 mi (4.1 km) away.

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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Things to do in North Shore

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Our top choices for Wingaersheek Beach hotels

1. Sally Webster Inn

2. The Rockport House

3. The Cove at Rockport Hotel

4. The Highliner Hotel

Top Wingaersheek Beach Hotel Reviews

Rockport Inn And Suites

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

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Clean Waterfront Classic Cottage with Private Beach

Oceanfront Dock Escape ~ Kayaks & Paddleboards

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

Evensong: Oceanview Retreat with Dock

Sunset Cove: Waterfront living on the Annisquam River

Waterfront Home with Spectacular Viewsof the Annisquam River

Hotels near other Wingaersheek Beach attractions

Cape Ann Museum

Dogtown

Plum Cove Beach

Paper House

Halibut Point Reservation

Gloucester Unitarian Universalist Church

Sargent House Museum

Frequently asked questions

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