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

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382 Best Vacation Rentals in Annisquam (Starting from $173)

Waterfront Escape Dock & More
Waterfront Escape Dock & More
House
Gloucester, MA, USA
0.7k from Annisquam center

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

4 Bedrooms12 Guests
New to Booking
$1025
Average price / night
Check Availability
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
0.4k from Annisquam 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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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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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
0.4k from Annisquam 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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OFFICIAL SITE - Buoy 23 Vacation Home Gloucester, MA Deepwater dock
OFFICIAL SITE - Buoy 23 Vacation Home Gloucester, MA Deepwater dock
House
Gloucester, MA, USA
2.2k from Annisquam 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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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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Big New England Family Home; walk to beach, shops
Big New England Family Home; walk to beach, shops
House
Rockport, MA, USA
4.3k from Annisquam center

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

9 Bedrooms16 Guests
10.0

Exceptional

1 reviews

$595
Average price / night
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Oceanside Estate: Main House & Apt w/beach access
Oceanside Estate: Main House & Apt w/beach access
House
Gloucester, MA, 01930, United States
0.9k from Annisquam center

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

4 Bedrooms10 Guests
New to Booking
$826
Average price / night
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Made for Beach Other
Made for Beach Other
House
Rockport, MA, USA
4.3k from Annisquam center

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

3 Bedrooms8 Guests
4.7

Review score

3 reviews

$322
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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Spacious 2nd floor Suite
Spacious 2nd floor Suite
Apartment
Gloucester, MA, USA
4.4k from Annisquam 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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BRAND NEW, Complete renovation: 4-Bedroom, 3.5 Bath, private Annisquam Gem!
BRAND NEW, Complete renovation: 4-Bedroom, 3.5 Bath, private Annisquam Gem!
House
Gloucester, MA, 01930, United States
1.0k from Annisquam center

Dryer, Heater, Internet, Laundry, No Smoking, Washer

4 Bedrooms12 Guests
New to Booking
$1105
Average price / night
Check Availability
Glorious Suite near Downtown with washer/dryer
Glorious Suite near Downtown with washer/dryer
Apartment
Gloucester, MA, USA
4.4k from Annisquam center

Parking, Internet, Security/Safety, Child Friendly

3 Bedrooms4 Guests
8.7

Fabulous

19 reviews

$291
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 Annisquam 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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Bianca's House
Bianca's House
House
Gloucester, MA, USA
4.4k from Annisquam 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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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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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 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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Vintage Rockport Escape
Vintage Rockport Escape
House
Rockport, MA, USA
4.5k from Annisquam center

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

3 Bedrooms6 Guests
8.3

Very Good

20 reviews

$364
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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Evensong: Oceanview Retreat with Dock
Evensong: Oceanview Retreat with Dock
House
Gloucester, MA, 01930, United States
1.2k from Annisquam 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
1.2k from Annisquam center

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

4 Bedrooms8 Guests
9.2

Superb

15 reviews

$504
Average price / night
Check Availability
Elegant Bayview Victorian Home; walk to beach
Elegant Bayview Victorian Home; walk to beach
House
Gloucester, MA, 01930, United States
1.3k from Annisquam center

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

6 Bedrooms12 Guests
9.0

Fabulous

2 reviews

$600
Average price / night
Check Availability
Guest House on Private Estate with Beach
Guest House on Private Estate with Beach
Apartment
Gloucester, MA, 01930, United States
1.3k from Annisquam center

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

2 Bedrooms6 Guests
New to Booking
$257
Average price / night
Check Availability
Timeless Seaside Estate: 4 Lodgings, Private Beach
Timeless Seaside Estate: 4 Lodgings, Private Beach
House
Gloucester, MA, 01930, United States
1.3k from Annisquam center

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

9 Bedrooms14 Guests
New to Booking
$3326
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 Annisquam.

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Frequently Asked Questions

You can explore 382 verified vacation rentals in Annisquam. 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 Annisquam 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 Annisquam 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 Annisquam 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 Annisquam 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.