Hotels near Wingaersheek Beach

Hotels near Wingaersheek Beach, Gloucester

Enter your dates for the latest hotel rates and availability.

Swipe up to view more
Filter by:
Hotel Star Rating
≤2345
Guest Rating
9+8+7+6+

Best Hotels near Wingaersheek Beach

Choose your travel dates to see the latest prices and deals.
Most Booked
Lowest Price
Closest to Downtown
Highest Rated
Stroll to SeaView/Beach; Great Yard Hotels near Wingaersheek Beach
Stroll to SeaView/Beach; Great Yard Hotels near Wingaersheek BeachStroll to SeaView/Beach; Great Yard Hotels near Wingaersheek Beach
2.39km from Wingaersheek Beach
The Ledge House is an idyllic retreat nestled in the heart of Gloucester's charming Bay View village. The historic farmhouse offers a taste of mid-19th-century charm, within step of the ocean.With private beaches, tennis courts, a playground, and access to an island via a granite causeway, there's no shortage of activities to enjoy during your stay. Enjoy the peaceful ambiance of the well-groomed yard with flower gardens and a dining area. It's the perfect place to unwind and recharge.About pets:No pets allowed.About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.About events:No events allowed.
Outstanding
5 reviews
10.0/10
Check Availability
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit Hotels near Wingaersheek Beach
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit Hotels near Wingaersheek BeachAntique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit Hotels near Wingaersheek Beach
2.23km from Wingaersheek Beach
- This cozy antique cottage with historic charm is in a quiet tucked away neighborhood of Gloucester - the perfect spot for a retreat- One of a kind SAUNA and fire pit in the backyard- Hi-speed WiFi- Plenty of off street parking spots- Fully equipped + stocked country kitchen with unique characteristics like an antique stove- A 10 minute drive to all the attractions of Downtown Gloucester- Walk to nearby hiking trails, beautiful Lighthouse Beach and the quaint village of Annisquam→ Warm and light filled sunroom with dining table to enjoy peaceful meals→ Roku TV equipped to stream all your favorites → 3 season sunroom porch with daybed closes off for an additional private sleeping space→ Living room with a pull out sofa also closes off for a third private sleeping space→ Plenty of off-street parking→ Fully equipped + stocked kitchen→ Outdoor shower and grill perfect for warmer days spent in the yard → Newly fenced in yard, perfect for your furry friends!PLEASE NOTE- The stairs are steep to the second floor so we don’t advise for anyone with mobility issues. There is a daybed and pull out sofa on the first floor. - The 3 season porch is not heated so it should only be used in warmer months! The sunroom is also 3 season but we provide a space heater for cooler months. *Rental Agreement is required to be signed after reservation has been confirmed. Failure to comply will result in the cancellation of reservation.*Damage Protection included - we have included a $28 charge in your total quote that covers your purchase of $1500 of "all risk" damage protection coverage on the rental property. This protection is purchased in lieu of a cash damage deposit. Coverage details are spelled out in the rental agreement. About pets:Pets allowed: dogs less than 20 lbs per pet (limit 2 pets total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Please pick up after your dog and dispose of their waste in the outside barrel. There is a puppy next door so please keep your dog on leash outside..No loud noise before 8am or after 10pm - we have great neighbors and we want to respect their space as well.,No candles or incense, and no smoking ANYTHING inside the house.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 20.About events:No events allowed.
Amazing
5 reviews
9.6/10
Check Availability
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat Hotels near Wingaersheek Beach
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat Hotels near Wingaersheek BeachDiscover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat Hotels near Wingaersheek Beach
2.47km from Wingaersheek Beach
Escape to our idyllic retreat, the ultimate vacation spot for you, your family, and friends. Nestled between the picturesque Annisquam Village and Lanesville, our turn-of-the-century Bayview home offers the perfect location to unwind and explore. Take a leisurely stroll to Plum Cove Beach for a day of sun and sand or venture up our street to enjoy a refreshing swim in the local quarry. A short walk brings you to the Greenbelt hiking trails or if you want to explore Dog Town it's just a short ride away. A mile from us is Halibut Point in Rockport.... There is so much to explore. As you step into our spacious and updated home, you'll be greeted by an inviting open living space and a new fully equipped kitchen, thoughtfully designed for comfort and relaxation. The first floor boasts a cozy bedroom with a queen bed, while the second floor features two additional bedrooms - one with a queen bed and the other with two twin beds with Ipswich Bay right across the way.Beyond the comforts of your temporary haven, a world of adventure awaits. Indulge in boating, whale watching, fishing, and swimming at breathtaking beaches. Embark on scenic sea kayaking excursions, explore the picturesque biking and hiking trails, and embark on leisurely nature walks. Immerse yourself in Cape Ann's vibrant art community, visit notable museums, and enjoy the lively atmosphere of festivals and farmer's markets.Let's not forget the "not to be missed" sunsets of Ipswich Bay (right across the street) or take a stroll to Plum Cove beach. And if you’re too relaxed to cook, Gloucester Center is just a seven-minute drive away and has a great selection of restaurants, bars & nightlife! (Don't forget to ask us for our recommendations!) Minutes to Rockport, and easily accessible by commuter rail or car from Boston -- less than an hour away.Escape to this Cape Ann sanctuary and experience the perfect blend of tranquility, natural beauty, and endless activities. This is the upstairs unit of a two family house (2nd and 3rd floors)Here's a glimpse of beautiful Gloucester:https://www.youtube.com/watch?v=63n9crVxhn0&fbclid=IwAR1__KZdtusK-B906mwogwSIg0pg0JtNoNHIrX8WeTUngly81JO3SjTjlBsSmoke and pet-free. Parking for two cars.Check-in 4pm, Checkout 10amAbout GloucesterGloucester, founded in 1623, is America's oldest seaport. It is the quintessential New England town. Among the many maritime activities offered by Gloucester are: world-class whale-watching expeditions, lighthouse tours, stunning destination beaches, the Gloucester Schooner Adventure, the Cape Ann Historical Museum, fishing and boating opportunities in abundance, the best seafood restaurants, and a lively nightlife rich with live music and theatre. Gloucester is also the home to National Geographic’s “Wicked Tuna”. And.....Wall Street Journal and Conde Nast say Gloucester and Cape Ann is a must-see!RESOURCESCape Ann Guide: https://issuu.com/bostonguide/docs/cacc_2020_web?fr=sYzFhNDcwOTADiscovery Gloucester: https://issuu.com/discovergloucester/docs/dg2020_fulllayoutrev2City of Gloucester website: https://gloucester-ma.gov/1074/Coronavirus-COVID-19More about Gloucester - https://www.onlyinyourstate.com/massachusetts/ancient-town-ma/?fbclid=IwAR0o9-XU4detObYU6lixK2EdIIpDFtWh7WXJ0v6ecaLwvLTOD5HUMPbEsz0FYI - The film CODA was filmed hereAbout pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:- No rearranging of furniture.- Close windows when leaving. Make sure deck umbrella is closed in the event of a change of weather. Turn off AC/heat when departing.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Outstanding
11 reviews
9.8/10
Check Availability
Gloucester
You Might Like
Gloucester Hotels With BreakfastGloucester Hotels With Twin RoomGloucester Hotels With 1 Double BedGloucester Hotels With Swimming PoolGloucester Hotels With Free Cancellation
Elegant Bayview Victorian Home; walk to beach Hotels near Wingaersheek Beach
Elegant Bayview Victorian Home; walk to beach Hotels near Wingaersheek BeachElegant Bayview Victorian Home; walk to beach Hotels near Wingaersheek Beach
2.25km from Wingaersheek Beach
Discover the historic charm of Bayview, a stunning private estate once home to Civil War General Benjamin F. Butler. Spanning 55 acres of meadows, forest, and rocky shoreline, it features two pristine beaches: a white-sand crescent and a mica-strewn gem. Nestled in the quaint village of Annisquam, this peaceful family compound offers access to Plum Cove Beach, Halibut Point State Park, and vibrant Gloucester and Rockport. Indulge in fresh seafood, coastal beauty, and timeless serenity.Immerse yourself in the beauty of the seaside at this expansive coastal home. Perfect for families or groups, the house comfortably sleeps up to 12 guests across six beautifully appointed bedrooms. For dining, the elegant dining room offers a touch of old-world charm, perfect for hosting memorable meals. The well-equipped galley kitchen provides everything you need to prepare, from simple snacks to gourmet feasts. Your stay includes access to two private beaches and tennis courts overlooking Ipswich Bay, ensuring endless opportunities for recreation and relaxation. For adventure lovers, the property also provides two adult and two child kayaks, inviting you to explore the waters nearby..About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
Outstanding
10.0/10
Check Availability
Private Beach!  Dream vacation at your private beach in Gloucester Hotels near Wingaersheek Beach
Private Beach!  Dream vacation at your private beach in Gloucester Hotels near Wingaersheek BeachPrivate Beach!  Dream vacation at your private beach in Gloucester Hotels near Wingaersheek Beach
2.42km from Wingaersheek Beach
Escape to this stunning private beach and enjoy this beach house with 3 bedroom. The ocean breeze and the sound of crashing waves will transport you to a serene oasis. Indulge in the luxurious amenities, including high-speed WiFi and a smart TV, perfect for cozy movie nights. Explore the local attractions, such as the Maritime Gloucester, the Shalin Liu Performance Center, and the captivating Hammond Castle, all within a short drive. Prepare delectable meals in the fully stocked kitchen, complete with a stove, oven, refrigerator, grill, and all the necessary appliances and utensils. Savor your culinary creations at the dining table, or step outside and fire up the grill for an alfresco feast right on the beach!. Unwind in the comfortable living room, or venture out to the balcony and bask in the breathtaking ocean views. Enjoy a full day of swimming, kayaking, paddle boarding, playing beach games or just sun bathing in a private beach well equipped with Beach gears so you don’t have to bring nothing to the beach!When it's time to relax gather around the fire pit for s'mores and stargazing. Enjoy the convenience of the in-unit washer and dryer, and keep the little ones entertained with the provided toys. With essentials like bathroom amenities, linens, and air conditioning, you'll have everything you need for a truly memorable vacation.About pets:No pets allowed.About checkOut:Check out before 10:30 AM.About children:Children allowed: ages 0-17.About customRules:At your check in please do a walkthrough the house and if you find that something is wrong or dirty, let host know right away so they can fix it..A waiver to use the beach need to be sign before arrival. After being at the beach, please rinse your feet before entering to the house.,No events or parties with your booking..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Amazing
9 reviews
9.6/10
Check Availability
Beach Life Bliss - steps to the beach Hotels near Wingaersheek Beach
Beach Life Bliss - steps to the beach Hotels near Wingaersheek BeachBeach Life Bliss - steps to the beach Hotels near Wingaersheek Beach
2.88km from Wingaersheek Beach
Delightful, dog friendly, 8 room romantic colonial home on beautifully landscaped lot just 5 doors from Plum Cove Beach. Get away from it all and watch the spectacular sunsets voted one of the best in the world by National Geographic. Be welcomed by the cobblestone Sun room, step thru a set of sliding glass doors to hardwood floors throughout the home. A full Kitchen with granite counters and stainless steel appliances will welcome and type of cooking from the advanced to the beginner. Relax after a day at the beach in our inviting dining and living room with a cozy wood stove for cold nights. Our basements holds the front loading washer and dryer for your use while at our beach house.Do not forget to go explore of Cape Ann; there are so many sites to see. You can enjoy Gloucester's rich New England history, natural beauty, extraordinary beaches, fresh seafood and on-water activities - especially the popular whale watching excursions, lighthouses, art galleries, fall foliage tours and other year round events. A truly charming 1900’s home; old details mixed with modern amenities in a wonderful beach community setting.Just the two of you: See our listing # 140506 on this site for our sister property. A luxurious cottage with all the amenities you could want.About pets:Pets allowed: dogs (limit 2 total).We welcome well behaved dogs.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.Unless discussed with property manager.About customRules:Please leave all the sand at the beach....Please remove all trash to outside bins, and clean and put away dishes before you go..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Outstanding
19 reviews
9.8/10
Check Availability
Evensong: Oceanview Retreat with Dock Hotels near Wingaersheek Beach
Evensong: Oceanview Retreat with Dock Hotels near Wingaersheek BeachEvensong: Oceanview Retreat with Dock Hotels near Wingaersheek Beach
1.35km from Wingaersheek Beach
Unobstructed Water Views of The Annisquam in this newly-renovated "walls of glass" home boasting panoramic views of The Mill River, Jones Creek, Wingaersheek Beach & beyond to the mountains of Maine. Deeded Water access available for enthusiastic kayakers or paddle boarders (please feel free to bring them with you). Enjoy our new dock (which is removed between November-April), shared with our neighbors below us. With a click of the remote cozy up to the gas fireplace & watch egrets, blue heron & cormorants as they glide over the water's surface all from the comfort of your home. Bask in the beauty of spectacular sunsets. Every day is a nature show! You won't miss a beat in this 1,600 square foot home with an open concept floor plan lending itself to views no matter where you are, even while preparing dinner in the Chef's kitchen featuring a Viking Stove, granite counters, back lit cabinetry & snack bar. Large composite deck with cable rail off the master bedroom overlooking the expanse of water. Young children would require supervision on the roofdeck. Our home features an outdoor grill, 3 bedrooms and 3 baths and sleeps 6-8. New washing machine and dryer on the first floor. It's a quick trip to the beach by paddleboard or kayak or a short drive to several local beaches, Halibut Point, more restaurants, museums, hiking, and quarries. Owners live locally and have a basement apartment (with separate entrance) at the property and will be available for questions/special requests. This is a perfect home for a friends or family retreat. Please no loud parties, as we live in a residential neighborhood.Off Season: 3-4 night minimum rental. Summer Season: Friday-Friday rental (7 night minimum)Smoke and pet-free. Parking for two cars.Boat docking (dock is tidal): $150/week payable through VenmoEV charging: $50/week payable through VenmoCheck-in 4pm, Checkout 11amAbout pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 3-17.6 and up preferred d/t roofdeck and outdoor stairs.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.Please no parties. residential neighborhood..
Outstanding
31 reviews
10.0/10
Check Availability
Walk to the ocean, very private. Secluded, woodsy location. Hotels near Wingaersheek Beach
Walk to the ocean, very private. Secluded, woodsy location. Hotels near Wingaersheek BeachWalk to the ocean, very private. Secluded, woodsy location. Hotels near Wingaersheek Beach
4.82km from Wingaersheek Beach
We are a cozy studio in a unique setting. There is a babbling brook that runs through the property to the ocean. This was a granite-quarrying site many years ago, and the property retains the remnants of a granite road used by ox carts to move granite blocks to the schooners. There is wild life on occasion, we recently had a great blue heron for several days. State park on the ocean is a 20 min walk.About pets:No pets allowed, service animals permitted.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:2 day minimum stay.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About events:No events allowed.
Outstanding
20 reviews
9.8/10
Check Availability
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC. Hotels near Wingaersheek Beach
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC. Hotels near Wingaersheek BeachShore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC. Hotels near Wingaersheek Beach
4.37km from Wingaersheek Beach
Shore Cottage is a newly renovated coastal inspired gem! Located near Gloucester’s famous boulevard and many other local hot spots. The cottage is behind the main house on the property, in a quiet and private residential neighborhood. A place to kick back and relax. Whether you’re in town for a wedding or just touring the area, this is an ideal spot to book for your next getaway!About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Fireplace is decorative only - not operational..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Outstanding
9.8/10
Check Availability
Glorious Suite near Downtown with washer/dryer Hotels near Wingaersheek Beach
Glorious Suite near Downtown with washer/dryer Hotels near Wingaersheek BeachGlorious Suite near Downtown with washer/dryer Hotels near Wingaersheek Beach
4.3km from Wingaersheek Beach
New to New England? Come stay at this peaceful, central, ground-level suite in downtown Gloucester! Enjoy walks to historic locations, public transit, as well as beaches, restaurants, and stores! Just an hour commute away from Boston, consider this as your new vacation home!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 28.About events:No events allowed.
Outstanding
2 reviews
10.0/10
Check Availability
Show More Hotels near Wingaersheek Beach

Top Pick Hotels near Wingaersheek Beach

See all
Discover our most booked hotels near Wingaersheek Beach from the last 30 days!
No.1
Castle Manor Inn Hotels near Wingaersheek Beach
8.1/10
101 review

Castle Manor Inn

Gloucester | 4.23KM from Wingaersheek Beach
"Good Location"
Select dates to view prices
No.2
The Hotel at Cape Ann Marina Hotels near Wingaersheek Beach
8.2/10
97 review

The Hotel at Cape Ann Marina

Gloucester | 4.46KM from Wingaersheek Beach
"Good Location"
Select dates to view prices
No.3
Beauport Hotel Gloucester Hotels near Wingaersheek Beach
9.6/10
100 review

Beauport Hotel Gloucester

Gloucester | 5.18KM from Wingaersheek Beach
"Good Location"
Select dates to view prices
No.4
Ocean House Hotel at Bass Rocks Hotels near Wingaersheek Beach
9.0/10
100 review

Ocean House Hotel at Bass Rocks

Gloucester | 6.72KM from Wingaersheek Beach
"Good Location"
Select dates to view prices

Frequently asked questions

What are the most popular hotels near Wingaersheek Beach?

How much does it cost to stay at a hotel near Wingaersheek Beach per night?

According to Trip.com, the average cost for a one-night stay at a hotel near Wingaersheek Beach in Gloucester is AU$249. Please note that prices fluctuate often, so this is a general guide only.

Which popular hotels near Wingaersheek Beach have pools?

Summer is the perfect time to cool off with a family getaway to Wingaersheek Beach in Gloucester. The Hotel at Cape Ann Marina (price from AU$367),Ocean House Hotel at Bass Rocks (price from AU$223) and Beauport Hotel Gloucester (price from AU$330) are some top hotels with pools where you can unwind and beat the heat.

What are the best hotels near Wingaersheek Beach with parking?

If you're planning a road trip to Gloucester Wingaersheek Beach, consider staying at Castle Manor Inn (price from AU$277),The Hotel at Cape Ann Marina (price from AU$367) and Harborview Inn (price from AU$323) , these hotels all offer parking.

What hotels near Wingaersheek Beach offer great breakfasts?

A good breakfast is all you need to kick-start your day. If you're after a hotel in Gloucester near Wingaersheek Beach with an excellent breakfast, you can consider staying Castle Manor Inn (price from AU$277),Harborview Inn (price from AU$323) and Ocean House Hotel at Bass Rocks (price from AU$223) .These hotels are very popular, so book early.

Which hotels near Wingaersheek Beach have gyms?

As people become more health-conscious, many hotels now include fitness rooms. Beauport Hotel Gloucester (price from AU$330) is a great option for hotels with fitness rooms.

How much does it cost to stay at hotels near Wingaersheek Beach this weekend?

According to Trip.com, the average cost for a one-night weekend stay at a hotel near Wingaersheek Beach in Gloucester is about AU$549. Prices can change often, so please use this as a general guide.

Which hotels near Wingaersheek Beach have free Wi-Fi?

Free and reliable Wi-Fi is a must when you're travelling. Castle Manor Inn (price from AU$277),The Hotel at Cape Ann Marina (price from AU$367) and Harborview Inn (price from AU$323) are all popular hotels that have free Wi-Fi.

Gloucester weather

Today
16 Nov, 2025
0
°
Mostly clear
Mostly clear 0 - 11℃
16 Nov, 2025
Mostly clearMostly clear
0 - 11℃
17 Nov, 2025
Intermittent cloudsIntermittent clouds
-1 - 6℃
18 Nov, 2025
Mostly clearMostly clear
1 - 7℃
19 Nov, 2025
Mostly clearMostly clear
0 - 6℃
20 Nov, 2025
OvercastOvercast
5 - 7℃
21 Nov, 2025
ShowersShowers
6 - 10℃
22 Nov, 2025
Intermittent cloudsIntermittent clouds
0 - 14℃

Gloucester Hotels near Wingaersheek Beach Information

Highest PriceAU$828
Lowest PriceAU$188
Number of Reviews 787
Total Properties38
Average Price(Weekday Night)AU$356
Average Price(Weekend Night)AU$384