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Cape Ann Vacation Rentals

Find 932 available house rentals from 11 partners
Anytime
1 guest
Anytime
1 guest

Top 15 Recommended vacation rentals in Cape Ann

Find your perfect vacation rental in Cape Ann from just $105 per night!

House Cape Ann
Jul 5 - Jul 12
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home with Yard, Terrace & BBQ

Cape Ann, North Shore, Massachusetts, United States
$356
per night
Outstanding(38 ratings)
$356
per night
View deal
Cottage Cape Ann
Aug 16 - Aug 23
Cottage ∙ 6 guests ∙ 3 bedrooms

Child-Friendly Lovely Cottage with Yard, BBQ & Terrace | City View | Beach Nearby

Cape Ann, North Shore, Massachusetts, United States
$377
per night
Outstanding(119 ratings)
$377
per night
View deal
Apartment Cape Ann
Jun 28 - Jul 5
Apartment ∙ 2 guests ∙ 1 bedroom

Children-Friendly Beautiful Holiday Apartment with BBQ & Garden | Nature View | Perfect for Remote Work

Cape Ann, North Shore, Massachusetts, United States
$105
per night
Outstanding(35 ratings)
$105
per night
View deal
Apartment Cape Ann
Jun 28 - Jul 5
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment with Barbeque & Terrace

Cape Ann, North Shore, Massachusetts, United States
$221
per night
Outstanding(36 ratings)
$221
per night
View deal
House Cape Ann
-17%
Jul 21 - Jul 28
House ∙ 6 guests ∙ 3 bedrooms

Children-Friendly Ample Vacation Home with Grill | Nature View | Perfect for Remote Work

Cape Ann, North Shore, Massachusetts, United States
$794$213
per night
Excellent(45 ratings)
$794$213
per night
View deal
Cottage Cape Ann
Jun 13 - Jun 20
Cottage ∙ 2 guests ∙ 1 bedroom

Cottage with Yard, Terrace & Grill

Cape Ann, North Shore, Massachusetts, United States
$211
per night
Outstanding(28 ratings)
$211
per night
View deal
House Cape Ann
Aug 2 - Aug 9
House ∙ 8 guests ∙ 4 bedrooms

Family-Oriented House with Barbecue & Terrace | Nature View | Perfect for Remote Work | Pets Allowed

Cape Ann, North Shore, Massachusetts, United States
$503
per night
Outstanding(6 ratings)
$503
per night
View deal
House Cape Ann
Jul 19 - Jul 26
House ∙ 10 guests ∙ 6 bedrooms

Child-Friendly Vacation Home with Barbeque & Patio | Nature View

Cape Ann, North Shore, Massachusetts, United States
$664
per night
Outstanding(79 ratings)
$664
per night
View deal
Apartment Cape Ann
Aug 23 - Aug 30
Apartment ∙ 5 guests ∙ 3 bedrooms

Family-Oriented Rental Apartment | City View | Beach Nearby

Cape Ann, North Shore, Massachusetts, United States
$216
per night
Excellent(116 ratings)
$216
per night
View deal
Apartment Cape Ann
-26%
Aug 29 - Sep 5
Apartment ∙ 4 guests ∙ 2 bedrooms

Wonderful Rental Apartment | City View

Cape Ann, North Shore, Massachusetts, United States
$462$150
per night
Outstanding(27 ratings)
$462$150
per night
View deal
House Cape Ann
Jun 14 - Jun 21
House ∙ 10 guests ∙ 4 bedrooms

Child-Friendly Beautiful House with BBQ, Patio & Garden | City View | Beach Nearby

Cape Ann, North Shore, Massachusetts, United States
$767
per night
Outstanding(82 ratings)
$767
per night
View deal
House Cape Ann
Mar 22 - Mar 29
House ∙ 4 guests ∙ 1 bedroom

Family-Friendly Spacious Vacation Home with Terrace & Barbecue | City View | Suitable for Remote Work | Pet-Friendly

Cape Ann, North Shore, Massachusetts, United States
$240
per night
Outstanding(33 ratings)
$240
per night
View deal
House Cape Ann
Jun 8 - Jun 15
House ∙ 10 guests ∙ 5 bedrooms

House with Grill, Terrace & Garden

Cape Ann, North Shore, Massachusetts, United States
$524
per night
Outstanding(24 ratings)
$524
per night
View deal
House Cape Ann
Jun 13 - Jun 20
House ∙ 7 guests ∙ 3 bedrooms

Vacation Home with Garden | Good for Workation

Cape Ann, North Shore, Massachusetts, United States
$261
per night
Outstanding(14 ratings)
$261
per night
View deal
Cottage Cape Ann
Jun 21 - Jun 28
Cottage ∙ 2 guests ∙ 1 bedroom

Cottage with Terrace

Cape Ann, North Shore, Massachusetts, United States
$142
per night
Excellent(110 ratings)
$142
per night
View deal

Apartments With Balconies or Patios

House  Cape Ann
Sep 14 - Sep 21
$319
per night
House ∙ 6 guests ∙ 2 bedrooms

Child-Friendly Wonderful House with Terrace | City View | Beach Nearby

5.0
Outstanding(4 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony/Patio
View deal
Apartment  Cape Ann
Jun 7 - Jun 14
$222
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment with Terrace & Grill | Nature View

5.0
Outstanding(153 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony/Patio
View deal
House  Cape Ann
Sep 14 - Sep 21
$209
per night
House ∙ 8 guests ∙ 5 bedrooms

Vacation Home with Terrace, BBQ & Garden | Nature View

4.0
Very good(32 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony/Patio
View deal
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Best Vacation Home Deals in Cape Ann

Save up to 67%

Cottage Cape Ann
May 3 - May 10
-41%
$538
$389
per night
Cottage ∙ 11 guests ∙ 5 bedrooms

Children-Friendly Cottage with Grill | Close to the Beach | Pets Allowed

Cape Ann, North Shore, Massachusetts, United States
Free cancellation
View deal
House Cape Ann
Mar 28 - Apr 4
-67%
$826
$329
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home with Barbecue & Patio

4.5
Excellent(147 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal
House Cape Ann
Apr 24 - May 1
-65%
$674
$209
per night
House ∙ 8 guests ∙ 5 bedrooms

Vacation Home with Terrace, BBQ & Garden | Nature View

4.0
Very good(32 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal

932 unique vacation homes from 11 vacation rental websites are available in Cape Ann, with prices beginning at $105 per night. HomeToGo immediately features the best offers by comparing all of the listed properties in Cape Ann from its various partners.

Budget-friendly Vacation Rentals in Cape Ann

Find Fantastic yet Inexpensive Offers

House Cape Ann
Jun 21 - Jun 28
$425
per night
House ∙ 4 guests ∙ 2 bedrooms

House with Patio & Grill | Suitable for Remote Work

5.0
Outstanding(36 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal
Cottage Cape Ann
Jun 14 - Jun 21
$219
per night
Cottage ∙ 3 guests ∙ 2 bedrooms

Cottage with Grill, Terrace & Yard | Nature View

5.0
Outstanding(136 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal
Cottage Cape Ann
Jun 21 - Jun 28
$199
per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Fully Equipped Lovely Cottage with Garden, Barbeque & Terrace

4.8
Outstanding(47 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal

Top-Rated Rentals and Accommodations in Cape Ann

Book Vacation Rental Offers with the Highest User Rating

House Cape Ann
Aug 9 - Aug 16
$482
per night
House ∙ 9 guests ∙ 5 bedrooms

Family-Oriented Vacation Home with Garden, Patio & BBQ | Nature View | Suitable for Remote Work

4.9
Outstanding(162 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal
House Cape Ann
May 15 - May 22
$231
per night
House ∙ 5 guests ∙ 2 bedrooms

Child-Friendly House | City View | Beach Nearby | Perfect for Remote Work | Pets Are Welcome

5.0
Outstanding(16 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal
House Cape Ann
Mar 28 - Apr 4
$405
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully Equipped Beautiful House with Barbecue, Terrace & Yard | Next to the Beach

4.5
Excellent(15 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal

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Popular Rental Amenities in Cape Ann

  • Pet-friendly (168)
  • Air conditioning (827)
  • WiFi (917)
  • Parking (21)
  • Pool (190)
  • Kitchen (611)
  • TV (792)
  • Balcony/patio (498)
  • Fireplace (329)
  • No smoking (890)
  • Grill (308)
  • Washing machine (322)

Many travelers spend more time comparing accommodations including pools. More than a fifth of the accommodations offer access to a pool. In addition, rentals with pools in Cape Ann have an average price of $414 per night. Most of the listed accommodations with pools are hotel room. In Cape Ann, more than half of the accommodations providing a pool are situated close to the water.

Enjoy fresh Atlantic air with a Cape Ann vacation rental

Just under an hour away from Boston, Cape Ann, Massachusetts, juts out into and overlooks the wide, glittering expanse of the Atlantic. Opt for a vacation home here to enjoy the beach setting, see whales play, and visit historical ports and some of America's most definitive Boston establishments.

What are the best activities for families in Cape Ann?

Go whale watching

Gloucester is ideally placed for whale watching, and the top observation spot is undoubtedly Stellwagen Bank National Marine Sanctuary. The area is a great place for diving expeditions, and there are cruises throughout the summer that grant you a good chance at spotting the region’s great whales. Kids love Cape Ann's most spectacular beach, Wingaersheek, overlooked by Annisquam Harbor Light Station, a historic lighthouse. You could also make a day trip to Stage Fort Park, which has two beaches and a recreation area with picnic tables, a playground, and hiking trails.

What are the best places to discover the arts and culture of Cape Ann?

Discover a 400-year-old port

Gloucester Harbor, a fishing port for 400 years, inspired works of fiction by Rudyard Kipling and the novel The Perfect Storm. Fishing boats still bob in the harbor, swamped in nets and other boating paraphernalia, just as they did in 1623 when the town was founded. Visit the Maritime Heritage Center, which restores wooden boats, and the popular Rocky Neck Art Colony, which boasts over a dozen galleries, studios, and restaurants. The artistic tradition of the community stems from that of Luminist painter and printmaker Fitz Henry Lane, a Gloucester inhabitant. See his works at the Cape Ann Museum.

Where are the unique attractions in Cape Ann?

Beautiful Boston

Boston is within easy reach. Come and see the country's first Ivy League school, Harvard. You can also learn about the city’s seminal role in gaining independence from Britain, which is commemorated along the Freedom Trail. Watch the mighty Red Sox play at Fenway Park, the nation's oldest ballpark. Alternatively, dine on local seafood and soak up the rich culture of the city.

Information about vacation rentals in Cape Ann

🏡 Vacation rentals available 932 rentals
💳 Possible discounts up to 67%
🌙 Nightly prices starting at $105
⭐ Popular amenities Pets allowed, Air conditioning and Internet
🐾 Pet friendly homes 168 homes
🏊 Vacation rentals with pools 190 homes
74,834 reviews
Cape Ann vacation rentals have an average rating of 4.6/5 on 74,834 reviews left by travelers.

Frequently Asked Questions

What is the average price per night for a vacation rental in Cape Ann?

The price of a night's stay in Cape Ann starts at $105. $656 is the average nightly price for house rentals in Cape Ann. Apartment rentals in Cape Ann cost on average $389 per night.

How many vacation rentals are available to book in Cape Ann?

Currently there are 932 vacation rentals available for booking for your upcoming trip.

What are the most popular amenities for vacation homes in Cape Ann?

The most popular amenities for vacation home rentals in Cape Ann include accommodations that have: Pets allowed, Air conditioning, and Internet.

How many vacation homes with a pool are there in Cape Ann?

Discover 190 vacation rentals available in Cape Ann.

Are pets allowed in vacation rentals in Cape Ann?

If you are traveling with a pet in Cape Ann - 18% of vacation rentals are pet-friendly.

What are the best months to travel to Cape Ann?

When choosing a vacation home in Cape Ann, keep in mind that rainy season is typically in December or February, with September often being the driest.

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