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Wingaersheek Beach, Gloucester, Massachusetts, United States of America
Photo by Kimi B

Wingaersheek Beach vacation rentals

We found 259 vacation rentals — enter your dates for availability

Discover a selection of 259 vacation rentals in Wingaersheek Beach that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $132 per night, and houses and cottages are popular options for a stay in Wingaersheek Beach. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Wingaersheek Beach
Stayed Oct 2021

Spacious, clean property

Rented this for a weekend getaway to Gloucester and Salem with NY husband and son. The property really was way bigger than we needed but it was walking distance to the beach and a short drive to the downtown area. The owner was very easy to communica...

Allison S.
Allison S.
Stayed Oct 2021

Great host, great location!!

Jonathan was amazing. Our flight was delayed and he picked up dinner for us and had it waiting since everything was closed. He also had the fridge stocked with beer wine and waters. I. Abbot say enough good things about this rental. We will definit...

Kim w.
Kim w.
Stayed Oct 2021

50th Birthday Celebration

Our time at Howard’s Cottage was amazing! This house is very well maintained, clean, and has all the amenities you could wish for. The beds were comfortable, plenty of towels for our use, linens included, and throws to keep us warm. The deck had amaz...

Lynn P.
Lynn P.
Stayed Oct 2021

Adorable Cottage

Janet's cottage was perfect for our stay in Rockport. It was walking distance to everything we wanted to see and Janet was a lovely host! The cottage was clean and had everything we needed for our stay. My boyfriend is 6'4 so some of the doorways and...

Jenna E.
Jenna E.
Stayed Sep 2021

Just wonderful

My wife and I hosted our family and everyone absolutely loved their stay. The view out of the wall of windows to Wingaerskeet Beach, Annisquam, and the Ipswich Bay is as good as it gets. We felt totally relaxed and had a great time exploring the Cape...

Russ C.
Russ C.
Stayed Sep 2021

Rockport sunrises

We really enjoyed our stay, especially watching sunrises from bed in the morning! The location was perfect for visiting Rockport, Gloucester, Essex, Salem... Google Maps was confused about the actual location of the house but got us close enough to f...

Lara B.
Lara B.
Stayed Sep 2021

A watery view

We were totally surprised on the unit's charm and spaciousness. The unit is a perfect setting and size for a family get together with one exception (limited parking ). The unit was very clean and well appointed. Our stay was very enjoyable and would ...

Sandy p.
Sandy p.
Stayed Sep 2021

Excellent stay!!

Our family vacation planned to cover many of New England's attractions. Beth was great. Our flight was changed at the last minute. Beth was totally accommodating and worked with us to allow early check-in. She was easy to reach and replied quickly. W...

Keith C.
Keith C.

Cincinnati OH

Find the best place to stay — Wingaersheek Beach

A tranquil ocean retreat steps from the water's edge

Sleeps 3 · 1 Bedroom · 1 Bathroom
$175 avg/night
(1)

Artist's Studio turned Guest House Sleeps up to 3

Sleeps 3 · Studio · 1 Bathroom
$132 avg/night
(102)

Sunset Views, Waterfront Property, Dock - Sleeps 12

Sleeps 12 · 4 Bedrooms · 2 Bathrooms
$263 avg/night
(42)

Good Harbor Beach House - Walk to Shops

Sleeps 7 · 3 Bedrooms · 1 Bathroom
$148 avg/night
(137)

Adorable Coastal Gem w/ Free WiFi, Private Gas Grill, Patio, & Easy Beach Access

Sleeps 4 · Studio · 1 Bathroom
$171 avg/night
(70)

Cozy Cottage Old Fashioned Charm

Sleeps 2 · 1 Bedroom · 1 Bathroom
$138 avg/night
(22)

Search 259 vacation rentals

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How many vacation rentals are available around Wingaersheek Beach?

Our 2021 property listings offer a large selection of 259 vacation rentals around Wingaersheek Beach. From 209 house rentals to 40 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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