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

Our top choices for Wingaersheek Beach hotels

Castle Manor Inn

4.1 km from Wingaersheek Beach

Junette

HK$1,832 total

includes taxes & fees

9 Jul - 10 Jul

Beauport Hotel Gloucester

Downtown Gloucester, 4.9 km from Wingaersheek Beach

Lucero

HK$3,492 total

includes taxes & fees

5 Jul - 6 Jul

Iron/ironing board, free WiFi, bed sheets

The Rockport House

5.7 km from Wingaersheek Beach

Kathleen

HK$1,524 total

includes taxes & fees

6 Jul - 7 Jul

The Cove at Rockport Hotel

5.2 km from Wingaersheek Beach

Tara

HK$2,818 total

includes taxes & fees

27 Jul - 28 Jul

Briar Barn Inn

17.5 km from Wingaersheek Beach

Aleese

HK$2,201 total

includes taxes & fees

6 Jul - 7 Jul

The Ipswich Inn

12.8 km from Wingaersheek Beach

Erik

HK$1,199 total

includes taxes & fees

7 Jul - 8 Jul

The Beverly

18 km from Wingaersheek Beach

Beth

HK$1,309 total

includes taxes & fees

27 Jul - 28 Jul

View all properties

Compare popular hotels close to Wingaersheek Beach

Property	Property class	Guest rating
Castle Manor Inn	2.5 star property	8.4 Very good 1,005 reviews	View
Beauport Hotel Gloucester	3.5 star property	9.6 Exceptional 976 reviews	View
The Rockport House	2.0 star property	9.4 Exceptional 214 reviews	View
The Cove at Rockport Hotel	2.5 star property	9.0 Wonderful 171 reviews	View
Briar Barn Inn	3.5 star property	9.6 Exceptional 826 reviews	View

Top Wingaersheek Beach Hotel Reviews

Castle Manor Inn

10/10 Excellent

"The Castle Manor Inn is a charming, family-owned property in a beautiful location with a gorgeous view of the Anasquam River. I had a last minute booking and got the last available room in the motel extension. At first I was disappointed not to get to stay in the beautiful Victorian house, but the motel is perched above the river and had a lovely view from the room and a private, covered area to sit outside and enjoy a beautiful summer evening with the sounds of birds and spring peepers, so the motel has its advantages! The AC kept the room nice and cool, and I was able to walk down to a restaurant on the marina for a wonderful seafood meal. The owner was so kind and friendly and gave me great local recommendations. It felt good to stay in a family-owned establishment where the owners take great pride in their inn and their community and genuinely enjoy interacting with their guests. The price was reasonable even as a last minute booking in the busy season. A great placed to stay all around!"

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."

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

10/10 Excellent

"Great place right on the water. There used to be a lobster business there. However, the Pappos' have done a great job of renovating and decorating. (Love the master bath.) The view is really the star of the show - with Annisquam Harbor right in front and the foot bridge to the village on the right. We walked to every place in Annisquam; and hung out on the porch in the mornings. We also rented a larger boat and was able to use the community dock (at high tide) on the bridge. The driveway was a little heart stopping 'cuz it is so steep. (You'll see) And the parking for our multiple cars tight. But just a wonderful place to hang with my brothers in a place (Annisquam) we hold dear to our family."

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!"

Oceanfront Dock Escape ~ Kayaks & Paddleboards

10/10 Excellent

"Superb location on the water with beautiful views from most of the rooms and all the living areas. Plus lovely sun deck. Slightly tricky entrance / exit, off the road but not a major hurdle. The house is airy, bright, clean, modern and a great place to relax. If sharing with friends, be aware that there are 3 private bedrooms, though plenty more bedding is available with sofa beds. We didn’t use the kayaks but at low tides there is a short but great bit of white water immediately by the house. Would certainly recommend for another holiday."

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.

See properties

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 25 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 25 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, Cogswell's Grant and Dogtown 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.

Explore a world of travel with Expedia

Things to do in North Shore

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Our top choices for Wingaersheek Beach hotels

Castle Manor Inn

Beauport Hotel Gloucester

The Rockport House

The Cove at Rockport Hotel

Briar Barn Inn

The Ipswich Inn

The Beverly

Compare popular hotels close to Wingaersheek Beach

Top Wingaersheek Beach Hotel Reviews

Castle Manor Inn

Rockport Inn And Suites

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Clean Waterfront Classic Cottage with Private Beach

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

Evensong: Oceanview Retreat with Dock

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

Oceanfront Dock Escape ~ Kayaks & Paddleboards

Sunset Cove: Waterfront living on 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

Explore a world of travel with Expedia