Best Vacation Homes in Annisquam
9 Guests
4 Bedrooms
2 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
R19,751/Night
For 7 Nights R138,259
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R3,877/Night
For 7 Nights R27,130
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R6,185/Night
For 7 Nights R43,297
1377.78 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
House
- Oceanfront
- Ocean View
- View
R6,427/Night
For 7 Nights R44,997
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
R4,439/Night
For 7 Nights R31,070
450 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
R4,483/Night
For 7 Nights R31,390
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R4,085/Night
For 7 Nights R28,595
Annisquam Luxury Rentals
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Parking
- Air Conditioner
- Child Friendly
R151,563/Night
For 7 Nights R1,060,942
14 Guests
9 Bedrooms
5 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R56,156/Night
For 7 Nights R393,087
R43,970/Night
For 7 Nights R307,791
16 Guests
8 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R28,587/Night
For 7 Nights R200,114
8 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R26,269/Night
For 7 Nights R183,880
2680.21 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Spa
- Fireplace/Heating
R25,467/Night
For 7 Nights R178,272
2682 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R25,367/Night
For 7 Nights R177,565
2300 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R22,821/Night
For 7 Nights R159,748
Annisquam Pet Friendly Vacation Rentals
1060 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R6,470/Night
For 7 Nights R45,284
796.53 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R4,833/Night
For 7 Nights R33,832
950 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R3,997/Night
For 7 Nights R27,972
1065.63 ft²
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
R6,029/Night
For 7 Nights R42,202
1181 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R12,909/Night
For 7 Nights R90,365
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
R4,034/Night
For 7 Nights R28,241
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R8,351/Night
For 7 Nights R58,453
800 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R6,284/Night
For 7 Nights R43,987
Annisquam Large Vacation Homes
12 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R7,233/Night
For 7 Nights R50,622
2497.23 ft²
10 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Private Beach
- Oceanfront
- Spa
R9,919/Night
For 7 Nights R69,433
2500 ft²
10 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R20,428/Night
For 7 Nights R142,991
1905.21 ft²
10 Guests
4 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- View
- Parking
R17,265/Night
For 7 Nights R120,863
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R12,697/Night
For 7 Nights R88,883
3500 ft²
14 Guests
6 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R19,751/Night
For 7 Nights R138,259
4000 ft²
18 Guests
10 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
R21,576/Night
For 7 Nights R151,024
1901 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R15,396/Night
For 7 Nights R107,761
Why Choose Rent By Owner for your Annisquam Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Annisquam
When should you plan your Vacation Rentals stay?
To make the most of your stay here, consider visiting during the shoulder seasons when the region offers pleasant weather and fewer crowds, allowing you to enjoy the tranquility and natural beauty that make this destination so appealing for vacation rentals.
Peak Season Highlights
Late Spring to Early Fall (May to September)
During these months, the area experiences warm weather and lively coastal activity, making it an ideal time to enjoy the region's natural beauty and outdoor pursuits.
Average Temperature Daytime: 70-80°F - Nighttime: 55-65°F
Summer (June to August)
This is the most popular season for visitors seeking sunny days and beachside adventures, perfect for exploring local sights and relaxing in scenic vacation rentals here.
Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F
Off-Season Highlights
Early Spring (March to April)
As the region transitions from winter, fewer travelers visit, offering a more tranquil experience while enjoying milder weather and blooming landscapes.
Average Temperature Daytime: 50-60°F - Nighttime: 40-50°F
Late Fall to Winter (October to February)
This quieter period features cooler temperatures and fewer visitors, providing a peaceful retreat with picturesque views and cozy stay options in this destination.
Average Temperature Daytime: 40-55°F - Nighttime: 30-40°F
Weekly Weather Forecast for Annisquam
How to Book Your Annisquam Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Annisquam
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor seating areas perfect for relaxing and dining al fresco amid scenic surroundings.
- Take advantage of private or shared garden spaces to unwind and connect with nature.
- Make the most of outdoor grills for cooking meals while enjoying the fresh air of this coastal region.
- Benefit from convenient parking options that make exploring the area effortless.
- Relax in a hammock or lounge chair on the patio while soaking in the local seaside ambiance.
- Explore nearby walking trails or pathways that lead to stunning views of the coastline and natural beauty.
- Utilize outdoor shower facilities, often available in beachside properties, to rinse off after days at the shore.
Top Attractions Around Annisquam
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities such as exploring scenic beaches, engaging in boating or fishing, and discovering local parks, all conveniently close to your vacation rental in Annisquam, Gloucester, Massachusetts.
Family Activities
- Annisquam Harbor Lighthouse Tour: Explore the historic lighthouse and learn about its significance in guiding maritime navigation along this coastal region.
- Crabbing and Clamming at Wingaersheek Beach: Enjoy a hands-on experience with your family by harvesting fresh crabs and clams in the tidal flats near the beach.
- Wander the Annisquam Village Green: Spend quality time strolling through the charming village green, taking in local shops, and soaking up the scenic seaside atmosphere.
- Family Day on Wingaersheek Beach: Relax and play together on the soft sands of this popular beach, ideal for building sandcastles and enjoying ocean views.
Adult Activities
- Explore the Annisquam River by Kayak: Enjoy a tranquil paddle along the calm waters surrounding the area, offering a peaceful way to experience the natural beauty of this coastal region.
- Visit the Annisquam Village Arts Center: Immerse yourself in local culture by exploring art exhibits and participating in workshops at this vibrant arts hub in the heart of the destination.
- Take a Scenic Drive Along the Coastline: Discover breathtaking ocean views and picturesque vistas as you navigate the scenic routes that highlight the region's rugged beauty.
- Relax on Wingaersheek Beach: Unwind on the soft sands of this popular nearby beach, where you can enjoy sunshine, gentle waves, and stunning sunset views just a short drive away.
Annisquam Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Waterfront Activities: Take advantage of the area's scenic waterways by engaging in boating, kayaking, or simply relaxing by the water to fully immerse yourself in this coastal destination.
- Visit Nearby Beaches: Make time to enjoy the nearby beaches, which offer a perfect setting for sunbathing, picnicking, or taking peaceful seaside strolls during your stay.
- Discover Charming Local Eateries: Savor the regional cuisine at local restaurants and cafes that showcase fresh seafood and authentic flavors unique to the region.
- Plan Outdoor Excursions: Utilize the natural beauty of here by exploring walking trails, parks, and scenic viewpoints to experience the region’s picturesque landscapes.
Transportation Options
- Gloucester Transportation Center: This central hub offers convenient train and bus services connecting you to nearby cities and airports, simplifying your travel planning around the region.
- Local Taxi Services: Reliable taxi companies in the area provide quick and comfortable transfers to local attractions, beaches, and transportation hubs during your stay.
- Rental Car Agencies: Several rental agencies operate nearby, giving you the freedom to explore here and beyond at your own pace with a private vehicle.
- Public Bus System: The regional bus network provides budget-friendly transportation options for easy access to Gloucester’s key sites and surrounding neighborhoods.
Local Customs Options
- Fishing Traditions: Locals here take pride in their long-standing fishing heritage, often observing quiet respect for the sea's bounty and participating in community fishing activities.
- Seafood Cuisine: Enjoy the local customs of preparing and sharing fresh seafood, which is a staple in the region’s dining experiences and a reflection of its maritime roots.
- Harbor Celebrations: The area hosts seasonal harbor festivities that celebrate maritime history, encouraging visitors to partake in the communal spirit and coastal traditions.
- Preservation of Historical Homes: Respect for the region’s historic architecture is common, with many residents maintaining traditional home styles that showcase local craftsmanship and history.
Frequently Asked Questions About Annisquam?
1. What are the top vacation rentals in Annisquam?
There are a lot of options in Annisquam. If you plan on staying in the Annisquam area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation 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
- Come home to Rockport!
- "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
2. How many vacation rentals have private pools in Annisquam?
There are 3 vacation rentals with private pools near Annisquam. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Annisquam are best for families?
If you are looking for a family-friendly vacation home in Annisquam, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Annisquam:
4. How many Rentbyowner vacation rentals are available in Annisquam?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 341 in the Annisquam area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Annisquam.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the property owner. You should review the specific listing details or contact the host directly to understand the terms and any potential fees associated with cancellations.
6. Are there any additional fees I should be aware of when booking a rental here?
Additional fees such as cleaning, service charges, or security deposits are typically listed on each property’s page. Check the listing thoroughly or reach out to the owner for precise fee details before completing your reservation.
7. How do I secure my reservation for a vacation rental in this region?
Reservations are usually secured through an online booking system. Make sure to follow the instructions provided in the listing and confirm your details with the property owner if necessary to ensure a smooth booking process.
8. What amenities are generally included in vacation rentals in the area?
Most rentals offer amenities like Wi-Fi, parking, and kitchen facilities, but specific inclusions can vary. Review the individual property listing to see which amenities are available during your intended stay.
9. What should I do if I encounter issues during my stay in a vacation rental here?
If problems arise, contact the property owner or local support team listed for the rental. They are there to assist you and ensure your experience remains positive.
Annisquam Top Rated Vacation Rentals
2501 ft²
6 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
R7,863/Night
For 7 Nights R55,034
1290 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
R9,217/Night
For 7 Nights R64,515
2300 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
R12,014/Night
For 7 Nights R84,101
R3,254/Night
For 7 Nights R22,785
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Pool
- Balcony/Terrace
- Breakfast
R2,615/Night
For 7 Nights R18,305
R4,221/Night
For 7 Nights R29,555
