We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Airbnb your place

Vacation rentals in Wingaersheek Beach

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Wingaersheek Beach

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Guest suite in Beverly

4.85 out of 5 average rating, 658 reviews

Historic North Shore, private suite & bathroom

Minutes from Salem! Relax in historic Beverly (walk to Beverly shops) in your private suite; bedroom, living room, and small bathroom, connected to our home, but private entrance. Just minutes from Salem. Commuter line to Boston and close to beautiful North Shore beaches and historic sites. Beaches within biking and driving distances, downtown, parks, hiking. Comfy, soft king bed, queen pull out couch, and plenty of linens. Great for couples, solo adventurers, business travelers, and families.

Aug 31 – Sep 7

ﺩ.ﺇ450 per night

Home in Gloucester

4.96 out of 5 average rating, 121 reviews

Booking spring/summer-Overlooking Lobster Cove

Booking spring, summer and fall 2024 now. Water views/access, sunsets above Lobster Cove on Washington St. Ideal for couple, NEW KING BED in master, queen in 2nd. Fast WiFi./TV. Not suitable for young children. Central A/C. 2nd fl unit large windows. Large open living/dining/kitchen area. Comfy new mattresses, 100% cotton sheets,sound machines. Overlooks beautiful Lobster Cove and footbridge. Minutes walk to the village of Annisquam and Lighthouse Beach. Small deck. Swim/kayak out your door.

Jan 2 – 9

ﺩ.ﺇ1,120 per night

Guest suite in Gloucester

4.94 out of 5 average rating, 35 reviews

Live Like a Local, Just Steps From The Beach

Beautiful and private 2 bedroom suite, located on the upper floor of stylish 19th century beach house. Steps (literally steps) from Plum Cove Beach and Lanes Cove you'll have choices of where to swim or watch the sunset over the water. Guests will have the entire 2nd floor, with a private entrance and is western facing for beautiful sunset views. Located within a 15 minute drive to downtown Rockport, Gloucester, Wingaersheek and Good Harbor Beaches. 30 minutes from Salem for Halloween fun!

Nov 26 – Dec 3

ﺩ.ﺇ332 per night

Guest suite in Gloucester

4.98 out of 5 average rating, 375 reviews

SplashLanding Private Beach Getaway in Gloucester

Jan-March 2024 open for monthly rentals. Must Book Summer 2024 via Airbnb website not the APP! *Our 2nd unit SquishInn has openings beginning April 2024 airbnb.com/h/squishinn-gloucester-ma Long walks on a private beach. Get sun-kissed; toes in the sand. Romantic dinners on the deck. Cozy in Winter (Energy Star home and Radiant heat throughout). TRAVELING WITH ANOTHER COUPLE? Book Private Beach Getaway SquishInn. Our 2nd unit for adult couples. Now another 2 friends can join you!

Dec 19 – 26

ﺩ.ﺇ1,051 per night

Guest suite in Peabody

4.98 out of 5 average rating, 177 reviews

Cozy West Peabody Guest Suite

Come enjoy this renovated studio guest suite in the quiet neighborhood of West Peabody! An easy drive to Salem or Boston, close to a woodsy bike trail, and a short drive to local shops and restaurants. Features a fully equipped kitchenette and an outdoor space with a fire pit and charcoal grill. Make use of a Roku TV and fast, reliable WiFi to keep yourself entertained. This is a great space whether you are looking to explore the Boston North Shore or simply embark on a quiet getaway.

Aug 11 – 18

ﺩ.ﺇ405 per night

Loft in Gloucester

4.9 out of 5 average rating, 167 reviews

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2024! We look forward to you visiting RockyNeck in Gloucester. You will be sure to enjoy various special activities and events this summer and fall. We are located in the "quiet end", on a private residential dead end street in a historic artist colony . Nearby public transportation, Audubon sites, cultural events, the Gloucester Stage Co and beaches . Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV

Jan 23 – 30

ﺩ.ﺇ451 per night

Cottage in Essex

4.97 out of 5 average rating, 212 reviews

French Flair "Pied a Terre" Cottage on the Marsh

Sunny cottage with marsh views, under 5 minute walk to town. Eat on the water in one of the many village restaurants, rent a kayak or paddle board. Go "down river" like a local! Shop the world renowned antique stores or enjoy the local beaches. There are many unique places to visit in Gloucester, Manchester, Rockport, Ipswich, Salem and of course Boston. There is a Visitor Manual for your convenience and we would be happy to answer questions that you might have.

Aug 22 – 29

ﺩ.ﺇ737 per night

Apartment in Ipswich

4.86 out of 5 average rating, 226 reviews

Confortable and confy , close to beach /sleeps 6

This home has all you need for your business or gateway in New England . With everything a Nice hotel has to offer ,this will be your home away from home. The Kitchen is fully equipped and you will have the entire place for yourself . You will be in walking distance to the train station in dowtown Ipswich and biking distance to the beach and Crane's Castle. Also you can explore Cannoing or paddling on the nearby Ipswich River.

Feb 26 – Mar 5

ﺩ.ﺇ524 per night

Guest suite in Rockport

4.99 out of 5 average rating, 609 reviews

Halibut Point State Park. Nature Lovers Retreat

"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.

Mar 16 – 23

ﺩ.ﺇ462 per night

Apartment in Rockport

4.9 out of 5 average rating, 144 reviews

Sweet short term rental in Rockport

Lovely hilltop unit located on private wooded property, steps away from 2 beaches. Built on a massive granite boulder, the property is one of kind with stunning seasonal views of the Atlantic. Fully equipped kitchen, flat screen TV, WiFi, and everything to make your stay pleasant and comfortable. We're a 7 minute drive from downtown Rockport and Gloucester, a 7 minute walk to Cape Hedge and Long Beaches.

Apr 20 – 27

ﺩ.ﺇ540 per night

Guest suite in Rockport

4.87 out of 5 average rating, 197 reviews

Charming Studio in the Pines

This is a first floor, above ground, garden apartment in a private home and is located in a quiet neighborhood with the backyard nestled in the woods, just out side your sliding door. Flower gardens and bird feeders adds ambiance for relaxing in a private setting. The studio offers a kitchenette, dining nook, a full bathroom, a queen bed, plus a sofa. Also available is CableTV, Netflix and Wi Fi.

May 8 – 15

ﺩ.ﺇ437 per night

Cottage in Gloucester

4.86 out of 5 average rating, 157 reviews

Bright & Cheerful 3BR+den, Gloucester Cottage

Quiet 3BR + den, 2BA cottage sits on a creek with a lovely deck overlooking the tidal marsh which opens up to Essex Bay. Comfy beds, light and airy space. Quiet neighborhood surrounded by nature. Train to Boston is 2 miles from the house, local hikes, bike rides and beaches all a short walk, drive or bike ride away.

Oct 2 – 9

ﺩ.ﺇ1,351 per night

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Wingaersheek Beach vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Wingaersheek Beach

Cottage in Gloucester

4.86 out of 5 average rating, 29 reviews

waterview guest suite

Nov 19 – 26

ﺩ.ﺇ590 per night

Cottage in Gloucester

4.97 out of 5 average rating, 100 reviews

Sunny & private cottage in Lanesville Village

May 5 – 12

ﺩ.ﺇ600 per night

Apartment in Gloucester

5.0 out of 5 average rating, 20 reviews

Cozy Apartment at Green Landing in Gloucester

Dec 31 – Jan 7

ﺩ.ﺇ554 per night

Condo in Gloucester

4.95 out of 5 average rating, 60 reviews

Luxurious beach house w/ harbor views & near beach

Apr 23 – 30

ﺩ.ﺇ568 per night

Guesthouse in Gloucester

4.94 out of 5 average rating, 34 reviews

Charming Guesthouse with Access to Private Beach

Nov 19 – 26

ﺩ.ﺇ928 per night

Home in Gloucester

4.83 out of 5 average rating, 23 reviews

Antique Cottage|PRIVATE SAUNA|Beach|Firepit+Grill

Apr 21 – 28

ﺩ.ﺇ764 per night

Condo in Ipswich

4.98 out of 5 average rating, 46 reviews

Private Ipswich Apartment

Dec 14 – 21

ﺩ.ﺇ576 per night

Guest suite in Gloucester

5.0 out of 5 average rating, 58 reviews

A charming Entire Guest Suite in Gloucester

May 15 – 22

ﺩ.ﺇ714 per night

Destinations to explore