Holiday rentals near Cape Ann

We found 436 holiday rentals — enter your dates for availability
Find the perfect private holiday rental within close proximity to Cape Ann. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as parking and a pool. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Cape Ann

Showing deals for:1 Jan - 8 Jan

Image gallery for Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 22

Updated kitchen with large island and plenty of counter space
9.6 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 22

Gloucester

8% off
Price is NZ$21,472
for 7 nights, 1 home
NZ$3,067 per night
includes taxes & fees
Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 22

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Why visit Cape Ann

  • Coastal Charm: Enjoy scenic ocean views and quaint seaside villages that capture the essence of New England's coastal beauty.
  • Rich History: Explore historic houses and landmarks that tell tales of Cape Ann's storied past.
  • Art and Culture: Discover local art galleries and cultural spots that celebrate the region's creative spirit.
  • Outdoor Adventures: Engage in family-friendly activities, from beach walks to nature reserves, perfect for all ages.
  • Local Flavour: Savour fresh seafood and local cuisine, offering a true taste of coastal living.

Top attractions near Cape Ann

Discover Cape Ann in Rockport, Massachusetts, where stunning beaches, serene reserve preserves, and historic houses await. Experience the charm of local culture and outdoor adventures, with iconic spots like the cape ann experience and dream cape ann. Enjoy a delightful blend of coastal beauty and history as you explore this unique destination, perfect for families, groups, or couples looking to immerse themselves in the local flavour.

  • Plum Cove Beach: Experience local beach vibes at this sandy escape 6km away, perfect for a relaxed day by the sea.
  • Essex River: Enjoy the outdoors along this scenic river 14km from Cape Ann, ideal for a refreshing nature walk.
  • Plum Island Sound: Visit this island getaway 21km off the coast, combining beach and outdoor experiences for a memorable coastal adventure.

Things to do recommended for couples

For a romantic escape in Cape Ann, explore the scenic beauty of Halibut Point State Park, enjoy a sunset cruise from Rockport Harbour, or indulge in a candlelit dinner at a charming seaside restaurant. Don't forget to wander through the picturesque streets hand-in-hand.

Things to do recommended for families

Families visiting Cape Ann can enjoy a day at the beautiful Halibut Point State Park, explore the charming shops in Rockport, and take a scenic boat tour to see the stunning coastline and local wildlife. Don't miss the chance to create lasting memories in this picturesque region.

Things to do recommended for groups

Groups visiting Cape Ann can enjoy a whale-watching tour, explore the vibrant art scene in Rockport, and savour fresh seafood at local eateries. Don’t miss hiking the scenic trails of Halibut Point State Park for breathtaking coastal views.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Cape Ann

If you're travelling with a group, family, or pets, or if you're considering longer stays, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Cape Ann with a group: Think about how many bedrooms you'll require, as well as any amenities like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Cape Ann with young kids: Traveling with young kids can be quite a task. It's important to prioritise their comfort and safety, alongside suitable facilities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Cape Ann: For many families, a trip isn’t truly complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Cape Ann: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Cape Ann

Exploring Cape Ann in Rockport, Massachusetts, offers a delightful coastal getaway filled with scenic beauty and rich history. Visitors can wander charming seaside villages, enjoy local art galleries, and savour fresh seafood while taking in stunning ocean views. The region's family-friendly atmosphere makes it perfect for excursions and relaxing moments alike. With its blend of adventure and culture, Cape Ann promises a memorable holiday experience that captures the essence of New England's coastal charm.

  • Gloucester: This vibrant city lies 6km from Cape Ann and offers a delightful mix of coastal charm and cultural attractions. Visitors revel in the scenic outdoors and sandy beaches, making it a perfect spot for enjoying seaside walks and appreciating natural beauty. Gloucester is celebrated for its arts centre and music concerts, providing a creative escape for those looking to immerse themselves in local culture. With its captivating family beach and nearby cape views, this destination is ideal for a leisurely exploration of both nature and community life.
  • Rockport: As the heart of Cape Ann, Rockport boasts an intimate connection with the sea and surrounding landscapes. This artistic town is known for its beach access and sweeping scenery, inviting travellers to explore its recreational areas and cultural venues. With opportunities for educational outings and music concerts, Rockport offers a well-rounded travel experience deeply rooted in coastal living. Its family beach and cape landmarks further enhance the allure of this destination, making it a wonderful place to enjoy outdoor adventures and artistic expressions.
  • North Shore: Located 8km from Cape Ann, North Shore is a vibrant destination that offers a rich blend of outdoor activities and family-friendly attractions. Whether you’re taking a gentle coastal stroll or exploring educational venues, the North Shore provides a refreshing escape with its scenic beach and lake views. The area also features accessible shopping centres that add a modern twist to its natural charm, making it a versatile choice for travellers seeking both relaxation and recreational experiences.

Best time to go to Cape Ann

If you're planning a trip to Cape Ann, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.1°F (-0.5°C)Light RainMostly SunnyAverage
February31.8°F (-0.1°C)Light RainMostly SunnyAverage
March36.7°F (2.6°C)Light RainMostly SunnyAverage
April45.1°F (7.3°C)Light RainMostly SunnyAverage
May54.3°F (12.4°C)Light RainMostly SunnyAverage
June62.4°F (16.9°C)Light RainMostly SunnyModerately High
July69.6°F (20.9°C)Light RainMostly SunnyModerately High
August69.4°F (20.8°C)Light RainMostly SunnyModerately High
September64.0°F (17.8°C)Light RainMostly SunnyAverage
October55.2°F (12.9°C)Light RainMostly SunnyModerately Low
November45.1°F (7.3°C)Light RainMostly SunnyModerately Low
December37.4°F (3.0°C)Light RainMostly SunnyModerately Low

Booking with Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s inventive Trip Board provides a dedicated area to build new trips, pick up where you last left off, or review and organise your plans. Any properties you’ve saved or booked before can now be found under Potential, Upcoming, or Current Trips. To explore the Trip Boards, please visit: https://www.bookabach.co.nz/trips

**Based on Vrbo properties bookings.

Frequently asked questions

What are the best holiday rentals near Cape Ann?
The best holiday rentals near Cape Ann are typically located in charming coastal towns like Rockport and Gloucester. You will find a great selection of properties, including private holiday houses great for families and stylish apartments close to the water. Choosing a rental a little further from the immediate coastline can also provide more affordable options. Guests looking for the best holiday rentals near Cape Ann will appreciate the variety available.

Many homes offer excellent amenities such as a deck or patio for enjoying the sea breeze, and laundry facilities for longer stays. These properties are ideal for families or groups seeking a comfortable base for exploring the coast.
Are there any cheap holiday rentals near Cape Ann?
There are several affordable holiday rentals near Cape Ann, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around NZ$ 320 per night in areas like Rockport. Some options might be found for less during March and April, which can be a good time to visit without overspending. These rentals often include free amenities such as WiFi, toiletries, and self-parking, providing a clean and comfortable base for guests.

To get the best value, consider staying slightly outside the main hubs of Cape Ann. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. Many of these budget-friendly properties are cosy and efficient, offering great value so you can have a comfortable stay near Cape Ann.

*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Cape Ann?
There are over 60 pet-friendly holiday rentals near Cape Ann, making it easy to include your dog in your plans. These properties are primarily private homes and cottages found in towns like Rockport, offering amenities such as private decks, easy outdoor access, and comfortable living spaces. These homes provide guests with comfort and convenience while ensuring their pets have ample space to relax.

When searching for the best pet-friendly holiday rentals near Cape Ann, it is important to check specific pet policies regarding fees or size restrictions. Cape Ann is generally pet-friendly, with many outdoor areas and trails where pets are welcome.
What are the top holiday rentals with pools near Cape Ann?
There are several holiday rentals near Cape Ann that include access to swimming pools, primarily featuring private outdoor pools. These properties are often found as private holiday houses in areas like Rockport and other coastal towns on Cape Ann. Many of these homes come equipped with standard amenities such as full kitchens, Wi-Fi, and outdoor spaces, making them well-suited for families or groups seeking a comfortable and convenient stay.

When selecting your rental, consider that private outdoor pools offer exclusive use and are great for families desiring seclusion. For stays during cooler months, checking for heated pool options is advisable to ensure maximum enjoyment.
What are the best family holiday rentals near Cape Ann?
There are over 117 family-friendly holiday homes available near Cape Ann, offering ample space and comfort for groups. These properties, predominantly private holiday houses and apartments, feature multiple bedrooms and bathrooms, full kitchens, and generous living areas. Many also include essential family amenities such as outdoor play areas, gardens, or secured yards, along with washer/dryers and entertainment options like WiFi and video games.

When selecting a home for your family, consider properties that provide separate spaces for adults and children, and prioritise those with well-equipped kitchens to simplify meal preparation. Staying close to Cape Ann means less daily travel, allowing more time to enjoy everything the area offers.
Are there any luxury holiday rentals near Cape Ann?
Near Cape Ann, guests can find several luxury holiday rentals that combine stunning scenery with modern comfort. These properties often feature upscale amenities such as private pools, private chefs, premium bedding, and lake views. Many homes also include air conditioning and fireplaces, ensuring a comfortable stay.

These homes are ideal for families or larger groups, offering spacious living areas. Many of these top-tier stays are managed by highly rated Bookabach hosts, ensuring a professional and premium experience.
How much is a holiday rental near Cape Ann?
Holiday rentals near Cape Ann offer a wide range of options suitable for different budgets, making it easy for guests to find a comfortable stay. Budget-friendly properties, such as simple apartments, typically start around NZ$ 320 per night, providing an affordable option to enjoy the area. Mid-range rentals, including private homes with standard amenities, are generally around NZ$ 651 per night, offering more space and comfort. For those seeking a more luxurious experience, upscale options can cost NZ$ 971 or more per night, often featuring premium amenities and prime locations.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.

*Pricing data are based on past 12 months data.
Where should I stay when visiting Cape Ann?
When visiting Cape Ann, guests have several excellent options for holiday rentals, each offering a great experience.

Rockport is a charming town on Cape Ann known for its picturesque harbour, Bearskin Neck, and art galleries. Staying in Rockport places you within easy reach of Motif No. 1 and various shops and eateries. Properties here often boast stunning ocean views and a quintessential New England coastal feel.

Gloucester, a historic fishing port, offers a more expansive selection of holiday rentals, from waterfront apartments to larger homes. It provides convenient access to beautiful beaches like Good Harbour Beach and Wingaersheek Beach, as well as whale watching excursions. Gloucester is a short drive from Cape Ann, making it a great base for exploring the entire peninsula.

For those seeking a quieter, more secluded experience, the residential areas around Annisquam or Lanesville offer lovely homes with a focus on natural beauty and tranquility. These areas provide a peaceful retreat while still being a convenient drive from the main attractions of Cape Ann.
What is the cheapest month to stay near Cape Ann?
The cheapest time to find holiday rentals near Cape Ann is typically during the early Spring (March-April). March is frequently the single cheapest month, often providing better deals on properties compared to the peak summer season. Guests can often find lower rates and greater availability during these months.
Are there any lakefront holiday rentals near Cape Ann
Lakefront holiday rentals near Cape Ann are readily available, primarily found on nearby freshwater bodies such as Chebacco Lake and Stiles Pond. These properties are a short drive from Cape Ann, offering convenient access to water activities like swimming, paddleboating, fishing, and motorboating, allowing guests to enjoy the tranquility of the lakes.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups seeking a comfortable stay.
Are there any top beachfront holiday rentals near Cape Ann
Beachfront holiday rentals near Cape Ann are primarily found along the scenic shores of Rockport and Gloucester, offering direct access to the sand or just steps from the water. Many properties boast ocean-view balconies, providing stunning vistas of the Atlantic. While some locations offer walkability to lively dining and shopping areas, quieter spots nearby provide a more relaxed environment for those seeking tranquillity.

Guests staying near Cape Ann can enjoy amenities such as beach chairs, umbrellas, and in some cases, oceanfront pools. Accommodation types range from cosy ocean-facing rooms to multi-bedroom units with private terraces, ideal for groups or longer stays.
Are there any monthly holiday rentals near Cape Ann?
Bookabach offers excellent options for monthly holiday rentals near Cape Ann, making it a great choice for those who want to combine work and adventure. Monthly rentals often feel like a true home away from home, with fully furnished properties equipped with essential amenities like high-speed Wi-Fi, full kitchens, and comfortable workspaces, perfect for remote work or a summer holiday with the family. With flexible monthly rental options, Bookabach is a convenient and comfortable choice for extended stays near Cape Ann.
Are there any last-minute holiday rentals near Cape Ann?
Bookabach makes it simple to find last-minute holiday rentals near Cape Ann that blend comfort, style, and great value. Bookabach offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars.

Finding these stays is easy. Just enter your destination and travel dates, then use Bookabach's "Last Minute" or "Discounts" filter to uncover the best offers. You'll see reduced rates in the listings. Bookabach's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting, you just have to decide where to go next.
Are all fees included in the Cape Ann holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any discounts for holiday homes near Cape Ann?
You can find great discounts on holiday homes near Cape Ann on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any holiday homes near Cape Ann with parking?
Bookabach offers a wide selection of holiday homes near Cape Ann with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I change or cancel my Cape Ann holiday home booking on Bookabach?
To find Cape Ann holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes near Cape Ann?
A long-stay holiday home near Cape Ann is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a holiday home near Cape Ann?
Book your Cape Ann holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home near Cape Ann?
Prices for holiday homes near Cape Ann vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes near Cape Ann to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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