Annisquam Holiday Rentals
- Massachusetts
- ·
- Rockport
- 0.07 mi to center
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
- Massachusetts
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- Gloucester
- 1.12 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Rockport
- 0.27 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
- Massachusetts
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- Gloucester
- 3.63 mi to center
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
- Massachusetts
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- Gloucester
- 1.33 mi to center
- Oceanfront
- Ocean View
- View
- Parking
- Massachusetts
- ·
- Gloucester
- 0.35 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Massachusetts
- ·
- Gloucester
- 0.87 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Rockport
- 0.84 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 4.55 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
Luxury Holiday Rentals in Annisquam
- Massachusetts
- ·
- Rockport
- 0.10 mi to center
- Parking
- Air Conditioner
- Child Friendly
- Security/Safety
- Massachusetts
- ·
- Gloucester
- 3.63 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Massachusetts
- ·
- Rockport
- 1.00 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Massachusetts
- ·
- Gloucester
- 3.84 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Massachusetts
- ·
- Gloucester
- 3.46 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Massachusetts
- ·
- Rockport
- 0.49 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
- Massachusetts
- ·
- Prides Crossing
- 8.80 mi to center
- Oceanfront
- Spa
- Fireplace/Heating
- Ocean View
- Massachusetts
- ·
- Prides Crossing
- 8.80 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Rockport
- 0.27 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
Top-Rated Holiday Rentals with a Pool in Annisquam
- Massachusetts
- ·
- Gloucester
- 1.56 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Massachusetts
- ·
- Rockport
- 0.47 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Massachusetts
- ·
- Gloucester
- 4.82 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Massachusetts
- ·
- Gloucester
- 1.42 mi to center
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
- Massachusetts
- ·
- Gloucester
- 1.49 mi to center
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
- Massachusetts
- ·
- Gloucester
- 1.38 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Massachusetts
- ·
- Gloucester
- 1.48 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Massachusetts
- ·
- Rockport
- 0.75 mi to center
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
- Massachusetts
- ·
- Gloucester
- 0.92 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
Pet-Friendly Holiday Rentals in Annisquam
- Massachusetts
- ·
- Rockport
- 0.39 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
- Massachusetts
- ·
- Gloucester
- 3.67 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
- Massachusetts
- ·
- Gloucester
- 4.56 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Rockport
- 0.40 mi to center
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
- Massachusetts
- ·
- Rockport
- 0.69 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Rockport
- 0.28 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 0.30 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Massachusetts
- ·
- Gloucester
- 3.67 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Rockport
- 0.25 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
Large Holiday Rentals and Private Villas in Annisquam
- Massachusetts
- ·
- Gloucester
- 2.38 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 3.17 mi to center
- Private Beach
- Oceanfront
- Spa
- Fireplace/Heating
- Massachusetts
- ·
- Gloucester
- 3.17 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 2.75 mi to center
- Fireplace/Heating
- View
- Parking
- Internet
- Massachusetts
- ·
- Rockport
- 0.43 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 2.75 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 1.96 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Massachusetts
- ·
- Gloucester
- 3.29 mi to center
- Fireplace/Heating
- Kitchen
- Parking
- Internet
- Massachusetts
- ·
- Rockport
- 1.08 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
Wheelchair Accessible Holiday Homes in Annisquam
- Massachusetts
- ·
- Gloucester
- 0.41 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 0.52 mi to center
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
- Massachusetts
- ·
- Gloucester
- 0.05 mi to center
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
- Massachusetts
- ·
- Gloucester
- 1.91 mi to center
- Kitchen
- Internet
- Wheelchair Accessible
- Laundry
- Massachusetts
- ·
- Rockport
- 0.74 mi to center
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 4.88 mi to center
- Balcony/Terrace
- Kitchen
- Child Friendly
- Wheelchair Accessible
- Massachusetts
- ·
- Gloucester
- 3.68 mi to center
- Balcony/Terrace
- Internet
- Wheelchair Accessible
- Laundry
- Massachusetts
- ·
- Gloucester
- 1.97 mi to center
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
Annisquam Private Villas and Holiday Homes Under $200
- Massachusetts
- ·
- Rockport
- 0.28 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
- Massachusetts
- ·
- Rockport
- 0.28 mi to center
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
- Massachusetts
- ·
- Rockport
- 1.94 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Rockport
- 0.78 mi to center
- Fireplace/Heating
- Child Friendly
- Restaurant
- Laundry
- Massachusetts
- ·
- Rockport
- 0.23 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 1.22 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
- Massachusetts
- ·
- Rockport
- 0.28 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Massachusetts
- ·
- Rockport
- 0.45 mi to center
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
- Massachusetts
- ·
- Rockport
- 0.24 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
Instantly Bookable Holiday Homes in Annisquam
- Massachusetts
- ·
- Rockport
- 0.85 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Massachusetts
- ·
- Rockport
- 0.49 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 0.41 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 2.05 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 1.33 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
- Massachusetts
- ·
- Rockport
- 0.38 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 1.22 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Rockport
- 0.28 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
- Massachusetts
- ·
- Rockport
- 0.10 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
Book a Last Minute Place to Stay in Annisquam
About Casai's Private Villas and Holiday Rentals in Annisquam
Discover more than 344 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 820.04 ft², with nightly prices averaging R9,347.
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.
Top Accommodation Types in Annisquam
| Type | Count |
|---|---|
| Vacation Homes | 228 |
| Holiday Apartments | 57 |
| Cottages | 31 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Annisquam
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Annisquam.
Weather in Annisquam, MA
View the weather forecast for Annisquam before booking your Annisquam Vacation Rentals to confirm your best time to go.
Frequently Asked Questions About Annisquam?
What are the top holiday rentals in Annisquam?
With numerous options available in Annisquam, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Annisquam:
- 4 Bedroom LUX House/with Pool Next Door
- Artist's Studio turned Guest House Sleeps up to 3
- WaterViews Overlooking Gloucester Inner Harbor/Sunroom/Deck/Walk to Town/AC
- Luxury Accommodations in Quiet Seaside Village
- Enjoy this cozy cottage with panoramic ocean views.
- "Absolutely lovely. The cottage, the beach, the town, the owners."
- Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck
- Sunset Views, Waterfront Property, Dock - Sleeps 12
- Elegant Gloucester Beach Getaway with Ocean Views!
- Luxury Home in the Heart of Rockport
How many holiday rentals have private pools in Annisquam?
Discover a selection of holiday rentals with private pools near Annisquam with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Annisquam are best for families?
If you're searching for a family-friendly holiday home in Annisquam, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Annisquam:
- "Absolutely lovely. The cottage, the beach, the town, the owners."
- Dog Friendly 2BR Home Walk to Beach+Bearskin Neck
- The Cove at Rockport Hotel
How many Casai.co.za holiday rentals are available in Annisquam?
As of 2026, Casai boasts over 344 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.








































































