Vacation Rentals in Wingaersheek Beach, MA: Compare 10+ Sites & Save

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  6.  Wingaersheek Beach

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389 Best Vacation Rentals in Wingaersheek Beach (Starting from $173)

Elegant Gloucester Beach Getaway with Ocean Views!
Elegant Gloucester Beach Getaway with Ocean Views!
House
Gloucester, MA, USA
0.8k from Wingaersheek Beach center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$589
Average price / night
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Clean Waterfront Classic Cottage with Private Beach
Clean Waterfront Classic Cottage with Private Beach
House
Gloucester, MA, 01930, United States
0.7k from Wingaersheek Beach center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms7 Guests
9.8

Exceptional

25 reviews

$402
Average price / night
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Waterfront Escape Dock & More
Waterfront Escape Dock & More
House
Gloucester, MA, USA
1.0k from Wingaersheek Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms12 Guests
New to Booking
$1025
Average price / night
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OFFICIAL SITE - Buoy 23 Vacation Home Gloucester, MA Deepwater dock
OFFICIAL SITE - Buoy 23 Vacation Home Gloucester, MA Deepwater dock
House
Gloucester, MA, USA
1.7k from Wingaersheek Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

4 Bedrooms7 Guests
New to Booking
$615
Average price / night
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Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam
House
Gloucester, MA, 01930, United States
0.8k from Wingaersheek Beach center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

6 Bedrooms15 Guests
9.4

Superb

61 reviews

$1020
Average price / night
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Airstream and Ocean View Unique Gloucester Getaway
Airstream and Ocean View Unique Gloucester Getaway
House
Gloucester, MA, USA
3.5k from Wingaersheek Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Glamping

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$287
Average price / night
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Wingaerchic: Woodsy retreat in West Gloucester
Wingaerchic: Woodsy retreat in West Gloucester
House
Gloucester, MA, 01930, United States
0.8k from Wingaersheek Beach center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
7.6

Good

4 reviews

$847
Average price / night
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Bianca's House
Bianca's House
House
Gloucester, MA, USA
4.0k from Wingaersheek Beach center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
6.0

Review score

3 reviews

$326
Average price / night
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Gull's Nest - Ocean Views from the Living Room
Gull's Nest - Ocean Views from the Living Room
House
Gloucester, MA, 01930, United States
0.9k from Wingaersheek Beach center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

4 Bedrooms10 Guests
New to Booking
$1160
Average price / night
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Spacious 2nd floor Suite
Spacious 2nd floor Suite
Apartment
Gloucester, MA, USA
4.1k from Wingaersheek Beach center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Self-catering, Beach rentals

2 Bedrooms4 Guests
7.1

Good

7 reviews

$173
Average price / night
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Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive
Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive
House
Gloucester, MA, 01930, United States
0.9k from Wingaersheek Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

66 reviews

$619
Average price / night
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Glorious Suite near Downtown with washer/dryer
Glorious Suite near Downtown with washer/dryer
Apartment
Gloucester, MA, USA
4.1k from Wingaersheek Beach center

Parking, Internet, Security/Safety, Child Friendly

3 Bedrooms4 Guests
8.7

Fabulous

19 reviews

$291
Average price / night
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VIEWS! Annisquam Bridge House at Lobster Cove. Booking Spring and Summer.
VIEWS! Annisquam Bridge House at Lobster Cove. Booking Spring and Summer.
Apartment
Gloucester, MA, 01930, United States
0.9k from Wingaersheek Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
9.8

Exceptional

29 reviews

$320
Average price / night
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Gloucester Getaway
Gloucester Getaway
House
MA, USA
4.1k from Wingaersheek Beach center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms7 Guests
New to Booking
$302
Average price / night
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NEW Rental: 2 min walk to Private Coffin's Beach
NEW Rental: 2 min walk to Private Coffin's Beach
House
Gloucester, MA, 01930, United States
0.9k from Wingaersheek Beach center

Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, TV, Washer

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$1099
Average price / night
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The Buoys
The Buoys
House
Gloucester, MA, USA
4.1k from Wingaersheek Beach center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$396
Average price / night
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Oceanfront Dock Escape ~ Kayaks & Paddleboards
Oceanfront Dock Escape ~ Kayaks & Paddleboards
House
Gloucester, MA, 01930, United States
1.0k from Wingaersheek Beach center

Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

5 reviews

$910
Average price / night
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Longview House
Longview House
House
Gloucester, MA, USA
4.3k from Wingaersheek Beach center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family, Accessible hotels

4 Bedrooms9 Guests
6.0

Review score

2 reviews

$383
Average price / night
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Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family
House
Gloucester, MA, 01930, United States
1.0k from Wingaersheek Beach center

AC, Arcade, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

6 Bedrooms15 Guests
9.4

Superb

26 reviews

$988
Average price / night
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Little River Retreat
Little River Retreat
House
Gloucester, MA, USA
4.3k from Wingaersheek Beach center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
6.0

Review score

1 reviews

$342
Average price / night
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Sunset Views, Waterfront Property, Dock - Sleeps 12
Sunset Views, Waterfront Property, Dock - Sleeps 12
House
Gloucester, MA, 01930, United States
1.0k from Wingaersheek Beach center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

4 Bedrooms12 Guests
10.0

Exceptional

97 reviews

$450
Average price / night
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Sunset Cove: Waterfront at Goose Cove
Sunset Cove: Waterfront at Goose Cove
House
Gloucester, MA, 01930, United States
1.0k from Wingaersheek Beach center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
8.8

Fabulous

22 reviews

$771
Average price / night
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Terra Nova Cottage Waterfront! Enjoy stunning views & sunsets over the Annisquam
Terra Nova Cottage Waterfront! Enjoy stunning views & sunsets over the Annisquam
House
Gloucester, MA, 01930, United States
1.0k from Wingaersheek Beach center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$515
Average price / night
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Evensong: Oceanview Retreat with Dock
Evensong: Oceanview Retreat with Dock
House
Gloucester, MA, 01930, United States
1.0k from Wingaersheek Beach center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

3 Bedrooms8 Guests
10.0

Exceptional

50 reviews

$594
Average price / night
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Amazing Waterfront/Access 4BDRM in Riggs Point
Amazing Waterfront/Access 4BDRM in Riggs Point
Cottage
Gloucester, MA, 01930, United States
1.0k from Wingaersheek Beach center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.2

Superb

15 reviews

$504
Average price / night
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Squam Light: Nestled in the heart of Annisquam
Squam Light: Nestled in the heart of Annisquam
House
Gloucester, MA, 01930, United States
1.1k from Wingaersheek Beach center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms9 Guests
7.0

Good

2 reviews

$714
Average price / night
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Beautifully renovated OCEAN-FRONT luxury home on private beach
Beautifully renovated OCEAN-FRONT luxury home on private beach
House
Gloucester, MA, 01930, United States
1.1k from Wingaersheek Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms8 Guests
New to Booking
$1362
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Wingaersheek Beach.

Wingaersheek Beach Vacation Rentals on the Map

Frequently Asked Questions

You can explore 389 verified vacation rentals in Wingaersheek Beach. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Wingaersheek Beach vary depending on the season, property size, and location. Rates typically start from around $173 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Wingaersheek Beach include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Wingaersheek Beach welcome pets. Currently, 32 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Wingaersheek Beach often include amenities such as Fireplace/Heating, View, and Laundry. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.