Vacation rentals in Cape Ann - HomeToGo base64Hash Vacation rentals in Cape Ann - HomeToGo

Vacation rentals in Cape Ann

Browse 698 available vacation homes and compared across 8 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Condo
    • House
    • Apartment

  • Rating

    • 4.5+
    • 4+

  • Services

    • Air conditioning
    • WiFi
    • Parking
    • Pool
    • Kitchen
    • TV
    • Balcony/patio
    • Fireplace
    • Washing machine
    • Yard
    • Microwave
    • Dishwasher
    • Hot tub
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Cape Ann

Discover your ideal Cape Ann vacation rental with real-time comparisons of 698 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Cape Ann
House ∙ 8 guests ∙ 4 bedrooms

House with garden, BBQ & patio | Suitable for remote work

Cape Ann, North Shore, Massachusetts, United States
This Gloucester house rental offers a fireplace, kitchen, yard, and parking, perfect for families of up to 8 guests.
from $792
per night
Outstanding(29 ratings)
from $792
per night
View deal
House Cape Ann
House ∙ 5 guests ∙ 2 bedrooms

Family-oriented house with yard, BBQ & terrace | City view | Next to the beach

Cape Ann, North Shore, Massachusetts, United States
This Gloucester house rental offers a kitchen, yard, and parking, perfect for families seeking a memorable getaway.
from $426
per night
Outstanding(21 ratings)
from $426
per night
View deal
House Cape Ann
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with barbecue

Cape Ann, North Shore, Massachusetts, United States
This Rockport house rental features a fireplace, kitchen, and parking, perfect for a memorable getaway with up to six guests.
from $841
per night
Outstanding(16 ratings)
from $841
per night
View deal
House Cape Ann
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, barbeque & yard

Cape Ann, North Shore, Massachusetts, United States
This Gloucester house rental features a kitchen, family-friendly yard, balcony, and parking, perfect for a memorable getaway.
from $485
per night
Excellent(19 ratings)
from $485
per night
View deal
House Cape Ann
House ∙ 9 guests ∙ 4 bedrooms

Vacation home with barbeque, terrace & yard

Cape Ann, North Shore, Massachusetts, United States
This Rockport house rental offers a yard, fireplace, and kitchen, perfect for families and pets, accommodating up to 9 guests.
from $313
per night
Outstanding(50 ratings)
from $313
per night
View deal
Cabin Cape Ann
Cabin ∙ 5 guests ∙ 2 bedrooms

Family-friendly cottage with patio, barbecue & yard | City view | Close to the beach | Pets are welcome

Cape Ann, North Shore, Massachusetts, United States
This Rockport cabin offers a kitchen, yard, and parking, making it perfect for a family getaway with your pets.
from $193
per night
Very good(54 ratings)
from $193
per night
View deal
House Cape Ann
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly nice vacation home | Next to the beach | Dogs allowed

Cape Ann, North Shore, Massachusetts, United States
This Rockport house rental offers waterfront access, a balcony, and a kitchen, perfect for family getaways with pets.
from $701
per night
from $701
per night
View deal
House Cape Ann
House ∙ 26 guests ∙ 11 bedrooms

Vacation home with hot tub, private pool & patio

Cape Ann, North Shore, Massachusetts, United States
This Gloucester house rental offers beach access, a heated pool, hot tub, and ample space for 26 guests to relax and unwind.
from $2,893
per night
Good(7 ratings)
from $2,893
per night
View deal
House Cape Ann
House ∙ 6 guests ∙ 2 bedrooms

Fully equipped vacation home with yard, terrace & private pool | Nature view | Next to the beach

Cape Ann, North Shore, Massachusetts, United States
This Rockport house rental features a pool, fireplace, and parking, accommodating up to six guests for an unforgettable getaway.
from $441
per night
Outstanding(5 ratings)
from $441
per night
View deal
House Cape Ann
House ∙ 7 guests ∙ 3 bedrooms

House with terrace, garden & BBQ

Cape Ann, North Shore, Massachusetts, United States
This family-friendly house in Gloucester features a cozy fireplace, a full kitchen, a spacious yard, and convenient parking for seven.
from $153
per night
Outstanding(125 ratings)
from $153
per night
View deal
House Cape Ann
House ∙ 10 guests ∙ 5 bedrooms

Family-oriented house with garden & terrace | Nature view | Good for workation

Cape Ann, North Shore, Massachusetts, United States
This waterfront house in Rockport features beach access, a yard, and a cozy fireplace, perfect for family gatherings of up to 10.
from $625
per night
Outstanding(176 ratings)
from $625
per night
View deal
House Cape Ann
House ∙ 11 guests ∙ 4 bedrooms

Vacation home with patio, barbecue & hot tub | Nature view

Cape Ann, North Shore, Massachusetts, United States
This house rental in Gloucester features a hot tub, fireplace, and a yard, perfect for a fun getaway with friends or family.
from $630
per night
Outstanding(53 ratings)
from $630
per night
View deal
House Cape Ann
House ∙ 18 guests ∙ 7 bedrooms

Vacation home with BBQ

Cape Ann, North Shore, Massachusetts, United States
This Gloucester house rental accommodates 18 guests, featuring a fireplace, parking, and a pet-friendly atmosphere for all.
from $1,823
per night
Outstanding(11 ratings)
from $1,823
per night
View deal
House Cape Ann
House ∙ 11 guests ∙ 5 bedrooms

Children-friendly vacation home with patio, grill & yard | Pets are welcome

Cape Ann, North Shore, Massachusetts, United States
This Gloucester house rental for 11 features a kitchen, fireplace, yard, and parking, perfect for family gatherings with pets.
from $646
per night
Outstanding(33 ratings)
from $646
per night
View deal
House Cape Ann
House ∙ 9 guests ∙ 4 bedrooms

Children-friendly beautiful house with terrace & barbeque | Next to the beach | Pet-friendly

Cape Ann, North Shore, Massachusetts, United States
This waterfront house in Rockport accommodates up to 9 guests, featuring beach access, a kitchen, and a balcony for relaxation.
from $650
per night
Outstanding(57 ratings)
from $650
per night
View deal

Vacation rentals and apartments with air conditioning

Cabin Cape Ann
from $259
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Fully equipped cottage with BBQ | Next to the beach

5.0
Outstanding(1 rating)
Cape Ann, North Shore, Massachusetts, United States
Air conditioning
View deal
House Cape Ann
from $413
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly house with BBQ, yard & patio | Nature view | Perfect for remote work | Pets allowed

4.9
Outstanding(73 ratings)
Cape Ann, North Shore, Massachusetts, United States
Air conditioning
View deal
Apartment Cape Ann
from $366
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental apartment | City view

5.0
Outstanding(6 ratings)
Cape Ann, North Shore, Massachusetts, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

House Cape Ann
from $511
per night
House ∙ 7 guests ∙ 3 bedrooms

House with terrace & BBQ | Nature view

5.0
Outstanding(46 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony/Patio
View deal
House Cape Ann
from $213
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with yard, BBQ & patio | Nature view

4.7
Excellent(45 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony/Patio
View deal
House Cape Ann
from $846
per night
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented house with terrace, yard & jacuzzi | Perfect for remote work | Dogs allowed

5.0
Outstanding(49 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony/Patio
View deal
See all offers

Vacation rentals with a balcony

House Cape Ann
from $412
per night
House ∙ 4 guests ∙ 2 bedrooms

Family-oriented vacation home with patio, BBQ & yard | Perfect for remote work

5.0
Outstanding(26 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony
View deal
House Cape Ann
from $758
per night
House ∙ 12 guests ∙ 5 bedrooms

Child-friendly house with yard, patio & barbecue | Nature view | Beach nearby

4.9
Outstanding(70 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony
View deal
House Cape Ann
from $665
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped wonderful house with grill & patio | Close to the beach

5.0
Outstanding(42 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Cape Ann offering exceptional value for money

Apartment Cape Ann
from $473
per night
Apartment ∙ 4 guests ∙ 1 bedroom

Rental apartment with BBQ, yard & terrace | Nature view

5.0
Outstanding(21 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal
House Cape Ann
from $165
per night
House ∙ 2 guests ∙ 1 bedroom

Vacation home | Perfect for remote work | Pet-friendly

Cape Ann, North Shore, Massachusetts, United States
View deal
House Cape Ann
from $428
per night
House ∙ 8 guests ∙ 3 bedrooms

House with garden, patio & barbecue

4.4
Very good(88 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal

Top-Rated Vacation rentals in Cape Ann

Book the highest-rated Cape Ann vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Cabin Cape Ann
from $571
per night
Cabin ∙ 8 guests ∙ 4 bedrooms

Family-friendly cottage with BBQ, patio & garden | Nature view

5.0
Outstanding(25 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal
House Cape Ann
from $352
per night
House ∙ 6 guests ∙ 3 bedrooms

House with garden, terrace & barbeque | Nature view

4.8
Outstanding(24 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal
Cabin Cape Ann
from $720
per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Children-friendly cottage with yard, patio & grill | Nature view | Close to the beach | Pets are welcome

4.9
Outstanding(18 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal

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Popular Features & Amenities in Cape Ann

  • Pet-friendly (119)
  • Air conditioning (610)
  • WiFi (650)
  • Parking (20)
  • Pool (165)
  • Kitchen (399)
  • TV (580)
  • Balcony/patio (477)
  • Fireplace (267)
  • No smoking (644)
  • Grill (288)
  • Washing machine (321)

Many travelers spend more time comparing accommodations including pools. More than a quarter of the accommodations offer access to a pool. In addition, rentals with pools in Cape Ann have an average price of $500 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.

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 698 rentals
💳 Possible discounts up to 25%
🌙 Nightly prices starting at $194
⭐ Popular amenities Pets allowed, Air conditioning and Internet
🐾 Pet friendly homes 106 homes
🏊 Vacation rentals with pools 175 homes

Frequently Asked Questions

What is the nightly price for a vacation rental in Cape Ann?

On average, vacation rentals in Cape Ann cost around $194 per night. $895 is the average nightly price for house rentals in Cape Ann. Apartment rentals in Cape Ann cost $435 per night on average.

How many vacation rentals are available for booking in Cape Ann?

There are 698 vacation homes from 8 different providers in Cape Ann.

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

Most travelers look for Pets allowed, Air conditioning, and Internet when booking a vacation rental in Cape Ann.

How many vacation homes with pools are there in Cape Ann?

Choose from 175 vacation rentals available in Cape Ann for renting.

Are dogs allowed in vacation rentals in Cape Ann?

Sure, there are 106 vacation homes in Cape Ann that allow pets and the average cost is $723 per night.

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