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

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  4.  Massachusetts

  5.  Gloucester
  6.  Wingaersheek Beach

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42 Best Cottage Rentals in Wingaersheek Beach (Starting from $141)

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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Summer Cottage on Ipswich Bay
Summer Cottage on Ipswich Bay
Cottage
Gloucester, MA, 01930, United States
2.7k from Wingaersheek Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

15 reviews

$664
Average price / night
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Bayview Guest Cottage
Bayview Guest Cottage
Cottage
Gloucester, MA, 01930, United States
2.7k from Wingaersheek Beach center

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

2 Bedrooms3 Guests
8.6

Fabulous

4 reviews

$448
Average price / night
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Luxury 1900's romantic retreat steps from the beach - King Suite!
Luxury 1900's romantic retreat steps from the beach - King Suite!
Cottage
Gloucester, MA, 01930, United States
2.8k from Wingaersheek Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

50 reviews

$339
Average price / night
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Private Cottage with AC & wifi, Steps to the Beach
Private Cottage with AC & wifi, Steps to the Beach
Cottage
Gloucester, MA, 01930, United States
3.3k from Wingaersheek Beach center

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

1 Bedroom2 Guests
New to Booking
$372
Average price / night
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Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Cottage
Gloucester, MA, 01930, United States
4.2k from Wingaersheek Beach center

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

1 Bedroom4 Guests
10.0

Exceptional

23 reviews

$381
Average price / night
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\"Absolutely lovely. The cottage, the beach, the town, the owners.\"
\"Absolutely lovely. The cottage, the beach, the town, the owners.\"
Cottage
Rockport, MA, 01966, United States
4.9k from Wingaersheek Beach center

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

2 Bedrooms7 Guests
10.0

Exceptional

109 reviews

$274
Average price / night
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You will love our location and will return for our hospitality!
You will love our location and will return for our hospitality!
Cottage
Rockport, MA, 01966, United States
5.0k from Wingaersheek Beach center

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

2 Bedrooms7 Guests
9.6

Exceptional

54 reviews

$260
Average price / night
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2BR Home Minutes to Downtown Rockport+Beach!
2BR Home Minutes to Downtown Rockport+Beach!
Cottage
Rockport, MA, 01966, United States
5.1k from Wingaersheek Beach center

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

2 Bedrooms5 Guests
10.0

Exceptional

12 reviews

$487
Average price / night
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Charming year round cottage - Pet Friendly with Wi-Fi
Charming year round cottage - Pet Friendly with Wi-Fi
Cottage
Rockport, MA, 01966, United States
5.1k from Wingaersheek Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

33 reviews

$570
Average price / night
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Charming Pet Friendly Studio Cottage On Quiet Lane
Charming Pet Friendly Studio Cottage On Quiet Lane
Cottage
Rockport, MA, 01966, United States
5.1k from Wingaersheek Beach center

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

10.0

Exceptional

17 reviews

$235
Average price / night
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Private Pet Friendly hideaway near the beach and town center.
Private Pet Friendly hideaway near the beach and town center.
Cottage
Rockport, MA, 01966, United States
5.1k from Wingaersheek Beach center

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

3 Bedrooms6 Guests
9.8

Exceptional

34 reviews

$507
Average price / night
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Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Cottage
Gloucester, MA, 01930, United States
5.2k from Wingaersheek Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

220 reviews

$614
Average price / night
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Sea Mist Cottage, Rockport, MA
Sea Mist Cottage, Rockport, MA
Cottage
Rockport, MA, 01966, United States
5.2k from Wingaersheek Beach center

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

1 Bedroom3 Guests
10.0

Exceptional

60 reviews

$234
Average price / night
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Cozy Cottage Old Fashioned Charm
Cozy Cottage Old Fashioned Charm
Cottage
Rockport, MA, 01966, United States
5.2k from Wingaersheek Beach center

AC, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio, TV

1 Bedroom2 Guests
9.4

Superb

98 reviews

$141
Average price / night
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Come home to Rockport!
Come home to Rockport!
Cottage
Rockport, MA, 01966, United States
5.3k from Wingaersheek Beach center

AC, Balcony, Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Microwave

1 Bedroom3 Guests
10.0

Exceptional

125 reviews

$205
Average price / night
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Cozy oceanfront home with unique architecture
Cozy oceanfront home with unique architecture
Cottage
Rockport, MA, 01966, United States
5.3k from Wingaersheek Beach center

AC, Dryer, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms3 Guests
7.6

Good

39 reviews

$355
Average price / night
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Quaint Waterfront Cottage
Quaint Waterfront Cottage
Cottage
Rockport, MA, 01966, United States
5.4k from Wingaersheek Beach center

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

1 Bedroom2 Guests
10.0

Exceptional

20 reviews

$217
Average price / night
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Ocean Views in this Charming 2 bedroom Cottage
Ocean Views in this Charming 2 bedroom Cottage
Cottage
Rockport, MA, 01966, United States
5.4k from Wingaersheek Beach center

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

2 Bedrooms5 Guests
10.0

Exceptional

7 reviews

$424
Average price / night
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cottage close to long beach and good harbor
cottage close to long beach and good harbor
Cottage
Gloucester, MA, 01930, United States
5.6k from Wingaersheek Beach center

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

3 Bedrooms5 Guests
New to Booking
$454
Average price / night
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Seaside Getaway Cottage w Deck, Parking, Ocean View, Shops
Seaside Getaway Cottage w Deck, Parking, Ocean View, Shops
Cottage
Rockport, MA, 01966, United States
5.6k from Wingaersheek Beach center

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

2 Bedrooms5 Guests
9.6

Exceptional

5 reviews

$415
Average price / night
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Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach
Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach
Cottage
Gloucester, MA, 01930, United States
5.7k from Wingaersheek Beach center

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

1 Bedroom4 Guests
9.8

Exceptional

105 reviews

$216
Average price / night
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Quaint & Cozy Rockport Gem ~ Walk to Sea ~ BBQ & Private Parking!
Quaint & Cozy Rockport Gem ~ Walk to Sea ~ BBQ & Private Parking!
Cottage
Rockport, MA, 01966, United States
5.9k from Wingaersheek Beach center

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

1 Bedroom2 Guests
9.8

Exceptional

9 reviews

$376
Average price / night
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Rockport Cottage w/ Patio - Steps to Beach!
Rockport Cottage w/ Patio - Steps to Beach!
Cottage
Rockport, MA, 01966, United States
5.9k from Wingaersheek Beach center

Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio

5 Bedrooms11 Guests
9.8

Exceptional

6 reviews

$446
Average price / night
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An Autumn Beach retreat - steps from ocean, drive to apple picking, local farms!
An Autumn Beach retreat - steps from ocean, drive to apple picking, local farms!
Cottage
Rockport, MA, 01966, United States
5.9k from Wingaersheek Beach center

Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$441
Average price / night
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Charming Coastal Cottage, Steps to Ocean & Rockport Village!
Charming Coastal Cottage, Steps to Ocean & Rockport Village!
Cottage
Rockport, MA, 01966, United States
5.9k from Wingaersheek Beach center

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

1 Bedroom2 Guests
9.8

Exceptional

16 reviews

$397
Average price / night
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Cottage House · Large Yard Fire Table · 6min walk · DNTN - New
Cottage House · Large Yard Fire Table · 6min walk · DNTN - New
Cottage
Rockport, MA, 01966, United States
6.0k from Wingaersheek Beach center

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

3 Bedrooms7 Guests
New to Booking
$714
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 Cottage Rentals in Wingaersheek Beach.

Wingaersheek Beach Cottage Rentals on the Map

Frequently Asked Questions

You can explore 42 verified cottage rentals in Wingaersheek Beach. Our listings are sourced from a range of trusted booking providers, giving you access to charming coastal cottages, peaceful countryside escapes, and cozy stays—all in one place.

Cottage rental prices in Wingaersheek Beach vary based on the season, location, and amenities offered. Rates typically start from around $141 per night, with higher prices during peak travel periods or in waterfront locations. Comparing different options can help you find a stay that fits both your preferences and budget.

Many cottages in Wingaersheek Beach feature inviting outdoor areas such as private gardens, patios, or small yards. These spaces are ideal for relaxing, dining outdoors, or enjoying the surrounding scenery. You can use the available filters to quickly find cottages with outdoor features that match your preferences.

Yes, cottages are often a great choice for travelers with pets thanks to their cozy layouts and access to outdoor space. Currently, 9 listings in Wingaersheek Beach welcome pets, making it easier to plan a comfortable stay with your companion.

For busy seasons such as summer holidays or long weekends, it’s a good idea to book your cottage 60 to 90 days in advance. Since cottages are typically smaller and more unique, the most desirable options tend to get reserved quickly during peak periods.

Cottages in Wingaersheek Beach are known for their comfort and charm, often including amenities such as Bedding/Linens, Kitchen, and Wellness Facilities. These features help create a relaxing and home-like atmosphere for guests.

Yes, many cottages in Wingaersheek Beach are well-suited for longer stays. They often include essentials like full kitchens, laundry facilities, and comfortable living spaces, making them a practical option for extended vacations or remote work.