Short-Term Rentals in Annisquam, MA: Compare 10+ Sites & Save

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393 Best Short-Term 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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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 Short-Term Rentals in Annisquam.

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Annisquam Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 393 verified short-term rentals in Annisquam, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Annisquam vary depending on location, property size, and travel dates. Rates typically start from around $173 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Annisquam include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Annisquam, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Annisquam often include amenities such as Fireplace/Heating, View, and Laundry, providing a comfortable and convenient stay.

Short-term rentals in Annisquam are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.