Oceanfront Rentals in Annisquam, MA: Compare 10+ Sites & Save

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  2. Oceanfront Rentals
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  4.  Massachusetts

  5.  Gloucester
  6.  Annisquam

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246 Best Oceanfront Rentals in Annisquam (Starting from $287)

Elegant Gloucester Beach Getaway with Ocean Views!
Elegant Gloucester Beach Getaway with Ocean Views!
House
Gloucester, MA, USA
1.3k from Annisquam 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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Squam Light: Nestled in the heart of Annisquam
Squam Light: Nestled in the heart of Annisquam
House
Gloucester, MA, 01930, United States
0.5k from Annisquam 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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Airstream and Ocean View Unique Gloucester Getaway
Airstream and Ocean View Unique Gloucester Getaway
House
Gloucester, MA, USA
4.1k from Annisquam 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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Oceanfront Dock Escape ~ Kayaks & Paddleboards
Oceanfront Dock Escape ~ Kayaks & Paddleboards
House
Gloucester, MA, 01930, United States
0.7k from Annisquam 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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Lovely Rockport Apartment, Walk to Beaches!
Lovely Rockport Apartment, Walk to Beaches!
Apartment
Rockport, MA, USA
4.4k from Annisquam center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

2 Bedrooms4 Guests
8.3

Very Good

10 reviews

$425
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
0.9k from Annisquam 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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The Buoys
The Buoys
House
Gloucester, MA, USA
4.6k from Annisquam 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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Cape Ann, Annisquam panoramic ocean views from every room.
Cape Ann, Annisquam panoramic ocean views from every room.
House
Gloucester, MA, 01930, United States
1.1k from Annisquam center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms11 Guests
9.6

Exceptional

43 reviews

$637
Average price / night
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Gloucester Home with Large Yard 1 Mi to Beach!
Gloucester Home with Large Yard 1 Mi to Beach!
House
Gloucester, MA, USA
4.9k from Annisquam center

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

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$474
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
1.2k from Annisquam 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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Walk to Front Beach Dtwn Rockport Retreat!
Walk to Front Beach Dtwn Rockport Retreat!
House
Rockport, MA, USA
5.0k from Annisquam center

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

3 Bedrooms8 Guests
New to Booking
$1053
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
1.2k from Annisquam 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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CbytheSea - Ocean View Penthouse
CbytheSea - Ocean View Penthouse
Apartment
Gloucester, MA, USA
5.1k from Annisquam center

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

1 Bedroom4 Guests
9.5

Superb

39 reviews

$507
Average price / night
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The Crow's Nest @ Rockport's Sail Loft
The Crow's Nest @ Rockport's Sail Loft
Apartment
Rockport, MA, USA
5.2k from Annisquam center

Apartments, Accommodations, Lodgings, Beach, Places to stay

1 Bedroom2 Guests
New to Booking
$483
Average price / night
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Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
House
Gloucester, MA, 01930, United States
1.3k from Annisquam center

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

4 Bedrooms7 Guests
9.8

Exceptional

12 reviews

$415
Average price / night
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Beach Gem
Beach Gem
House
Gloucester, MA, USA
5.7k from Annisquam center

Air Conditioner, Security/Safety, Parking, Ocean View, View, Oceanfront, Internet

3 Bedrooms5 Guests
8.6

Fabulous

11 reviews

$482
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
1.4k from Annisquam 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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Rockport Cottage with Patio - Steps to Beach!
Rockport Cottage with Patio - Steps to Beach!
House
Rockport, MA, USA
5.7k from Annisquam center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

5 Bedrooms11 Guests
9.0

Fabulous

2 reviews

$752
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
1.4k from Annisquam 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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Robbins Island Retreat
Robbins Island Retreat
House
Essex, MA, USA
5.8k from Annisquam center

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

2 Bedrooms4 Guests
New to Booking
$339
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
1.4k from Annisquam 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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Helena House: Close to Plum Cove Beach
Helena House: Close to Plum Cove Beach
House
Gloucester, MA, 01930, United States
1.5k from Annisquam center

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

3 Bedrooms7 Guests
8.2

Very Good

12 reviews

$678
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
1.6k from Annisquam 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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Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access
Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access
House
Gloucester, MA, 01930, United States
1.6k from Annisquam center

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

5 Bedrooms11 Guests
9.8

Exceptional

22 reviews

$595
Average price / night
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Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
House
Gloucester, MA, 01930, United States
1.6k from Annisquam center

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

4 Bedrooms8 Guests
9.8

Exceptional

39 reviews

$623
Average price / night
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Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat
Apartment
Gloucester, MA, 01930, United States
1.7k from Annisquam center

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

3 Bedrooms6 Guests
9.8

Exceptional

122 reviews

$376
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
2.1k from Annisquam center

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

2 Bedrooms4 Guests
9.8

Exceptional

50 reviews

$339
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 Oceanfront Rentals in Annisquam.

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Annisquam Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 246 verified oceanfront rentals in Annisquam. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Annisquam vary depending on the property size, exact beachfront location, and season. Rates typically start from around $287 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Annisquam offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Annisquam welcome pets. Currently, 28 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Annisquam often include features designed for a comfortable coastal stay, such as Ocean View, Oceanfront, and View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.