Annisquam Holiday Rentals

Compare Villas, Resorts, & Rentals in Annisquam, Gloucester, Massachusetts, USA

The Buoys
FromZA R6,552 per night
|
10.0 (7 Reviews)
3 Bedrooms 6 Guests
Addison Choate Inn
FromZA R3,809 per night
|
9.8 (377 Reviews)
1 Bedroom 2 Guests
1 Mi to Beach! Family Gloucester Gem with Yard
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10.0 (2 Reviews)
2 Bedrooms 6 Guests
Lantana House
FromZA R4,463 per night
|
9.4 (65 Reviews)
1 Bedroom 2 Guests
Artist's Studio turned Guest House Sleeps up to 3
10.0 (168 Reviews)
1 Bedroom 3 Guests
Elegant Gloucester Beach Getaway with Ocean Views!
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10.0 (1 Review)
5 Bedrooms 10 Guests
Rockport Inn And Suites
FromZA R2,569 per night
8.6 (1556 Reviews)
1 Bedroom 2 Guests
Luxury Accommodations in Quiet Seaside Village
10.0 (130 Reviews)
1 Bedroom 2 Guests
Waterfront Escape Dock & More
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10.0 (1 Review)
4 Bedrooms 10 Guests
Come home to Rockport!
FromZA R3,678 per night
10.0 (125 Reviews)
1 Bedroom 3 Guests
Airstream and Ocean View Unique Gloucester Getaway
|
10.0 (1 Review)
2 Bedrooms 4 Guests
"Absolutely lovely. The cottage, the beach, the town, the owners."
10.0 (109 Reviews)
2 Bedrooms 7 Guests
Big New England Family Home; walk to beach, shops
10.0 (1 Review)
9 Bedrooms 16 Guests
A tranquil ocean retreat steps from the water's edge
10.0 (102 Reviews)
1 Bedroom 3 Guests
The Beech Tree B&B
FromZA R3,392 per night
|
9.6 (18 Reviews)
3 Bedrooms 6 Guests
Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck
10.0 (100 Reviews)
1 Bedroom 2 Guests
Gloucester Harbor Hideaway
FromZA R9,552 per night
|
9.4 (5 Reviews)
2 Bedrooms 4 Guests
Sea Mist Cottage, Rockport, MA
FromZA R3,651 per night
10.0 (60 Reviews)
1 Bedroom 3 Guests
Lantana House
FromZA R4,120 per night
|
9.1 (57 Reviews)
4 Bedrooms 8 Guests
WATERFRONT 1BDRM SPACIOUS STUDIO APARTMENT
10.0 (48 Reviews)
1 Bedroom 2 Guests
Massachusetts Abode with Deck and Grill Near Beaches!
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9.0 (6 Reviews)
2 Bedrooms 4 Guests
Vintage Rockport Escape
FromZA R5,924 per night
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8.7 (20 Reviews)
1 Bedroom 6 Guests
Gloucester Home w/Large Yard: 1 Mi to Beach!
10.0 (34 Reviews)
2 Bedrooms 6 Guests
Lovely Rockport Apartment, Walk to Beaches!
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7.8 (11 Reviews)
2 Bedrooms 4 Guests
Rustic Rockport Cottage
FromZA R3,177 per night
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6.9 (9 Reviews)
2 Bedrooms 3 Guests
Seaside Village of Lanesville - North Gloucester, MA
10.0 (30 Reviews)
2 Bedrooms 4 Guests
Bianca's House
FromZA R5,394 per night
6.5 (4 Reviews)
1 Bedroom 4 Guests
The View: The Name Says It All
10.0 (26 Reviews)
2 Bedrooms 6 Guests
Longview House
FromZA R6,346 per night
|
6.0 (2 Reviews)
1 Bedroom 9 Guests
Adorable renovated house, steps from Front Beach and Town
10.0 (26 Reviews)
2 Bedrooms 4 Guests
Little River Retreat
FromZA R5,667 per night
|
6.0 (1 Review)
2 Bedrooms 4 Guests
Made for Beach Other
FromZA R5,042 per night
4.7 (3 Reviews)
1 Bedroom 8 Guests
Quaint Waterfront Cottage
FromZA R3,696 per night
10.0 (20 Reviews)
1 Bedroom 2 Guests
La Casa De La Playa
FromZA R25,020 per night
|
New
5 Bedrooms 10 Guests
Charming Pet Friendly Studio Cottage On Quiet Lane
10.0 (17 Reviews)
1 Bedroom 2 Guests
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
10.0 (12 Reviews)
1 Bedroom 4 Guests
Airstream & Ocean View: Unique Gloucester Getaway
10.0 (10 Reviews)
2 Bedrooms 4 Guests
Ocean Views in this Charming 2 bedroom Cottage
10.0 (7 Reviews)
2 Bedrooms 5 Guests
Sea Glass House - Tranquil Retreat or Base for Adventure
10.0 (4 Reviews)
2 Bedrooms 5 Guests
Granite Cottage: Pigeon Cove Delight
9.2 (9 Reviews)
1 Bedroom 4 Guests
Pine House
FromZA R6,621 per night
|
New
1 Bedroom 4 Guests
The Highliner Hotel
FromZA R5,857 per night
10.0 (1 Review)
1 Bedroom 2 Guests
Lovely Rockport Apartment, Walk to Beaches!
9.0 (13 Reviews)
2 Bedrooms 4 Guests
4BR Home | Walk to Beach & Downtown | Parking
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New
4 Bedrooms 8 Guests
The Vista
FromZA R3,978 per night
9.4 (418 Reviews)
1 Bedroom 2 Guests
Sunset Cove: Waterfront at Goose Cove
8.8 (22 Reviews)
2 Bedrooms 6 Guests
Sea Lion Motel and Cottages
9.2 (448 Reviews)
1 Bedroom 2 Guests
Bayview Guest Cottage
FromZA R6,001 per night
8.6 (4 Reviews)
2 Bedrooms 3 Guests
Gloucester Getaway
FromZA R4,997 per night
|
New
1 Bedroom 7 Guests
Cozy oceanfront home with unique architecture
7.6 (39 Reviews)
2 Bedrooms 3 Guests
Do not use this property
FromZA R148,907 per night
New
1 Bedroom 5 Guests
Refreshing Ocean View comfort space
New
3 Bedrooms 6 Guests
Portside Overlook: Village and Beach Views!
New
2 Bedrooms 5 Guests
Yankee Clipper Inn
FromZA R43,199 per night
|
9.1 (121 Reviews)
14 Bedrooms 7 Guests

About Casai's Private Villas and Holiday Rentals in Annisquam

Discover more than 330 vacation rentals available in Annisquam. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Annisquam.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Annisquam, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Annisquam. On average, places to stay near Annisquam offer 831.22 ft², with nightly prices averaging ZA R8,354.

With Casai, finding and comparing holiday rentals in Annisquam is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Frequently Asked Questions About Annisquam?

What are the top holiday rentals in Annisquam?

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As of 2026, Casai boasts over 330 properties listed in the Annisquam area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Annisquam.