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

Vacation rentals in Cape Ann

Browse 736 available vacation homes and compared across 11 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 736 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Cabin Cape Ann
Cabin ∙ 8 guests ∙ 4 bedrooms

Cottage with terrace, garden & BBQ | City view

Cape Ann, North Shore, Massachusetts, United States
This Gloucester cabin features a kitchen, yard, and parking, perfect for families and pets, accommodating up to 8 guests.
from $378
per night
Outstanding(264 ratings)
from $378
per night
View deal
House Cape Ann
House ∙ 8 guests ∙ 3 bedrooms

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

Cape Ann, North Shore, Massachusetts, United States
This Rockport house rental for 8 features a fireplace, hot tub, kitchen, and a yard, perfect for family gatherings with pets.
from $787
per night
Outstanding(49 ratings)
from $787
per night
View deal
Apartment Cape Ann
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with barbecue, yard & patio | Perfect for remote work

Cape Ann, North Shore, Massachusetts, United States
This Gloucester apartment features a fireplace, kitchen, yard, and parking, perfect for a family getaway with room for four.
from $140
per night
Outstanding(26 ratings)
from $140
per night
View deal
House Cape Ann
House ∙ 10 guests ∙ 4 bedrooms

Child-friendly house with BBQ & patio | City view | Suitable for remote work

Cape Ann, North Shore, Massachusetts, United States
This waterfront house rental in Gloucester features a kitchen, balcony, and parking, perfect for families of up to 12.
from $600
per night
Outstanding(9 ratings)
from $600
per night
View deal
Apartment Cape Ann
Apartment ∙ 4 guests ∙ 1 bedroom

Rental apartment with patio, barbeque & yard | Nature view

Cape Ann, North Shore, Massachusetts, United States
This Gloucester apartment rental features a kitchen, yard, and parking, making it perfect for families and pets alike.
from $132
per night
Outstanding(118 ratings)
from $132
per night
View deal
House Cape Ann
House ∙ 3 guests ∙ 1 bedroom

Children-friendly beautiful vacation home with barbeque & patio | Nature view

Cape Ann, North Shore, Massachusetts, United States
This waterfront house rental in Gloucester features a kitchen, parking, and is perfect for a family getaway with three guests.
from $190
per night
Outstanding(99 ratings)
from $190
per night
View deal
Apartment Cape Ann
Apartment ∙ 3 guests ∙ 1 bedroom

Rental apartment with patio, garden & barbeque | Perfect for remote work

Cape Ann, North Shore, Massachusetts, United States
This waterfront apartment in Gloucester features a kitchen, yard, and parking, perfect for a getaway with friends or family.
from $211
per night
Outstanding(115 ratings)
from $211
per night
View deal
House Cape Ann
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with yard, barbeque & terrace

Cape Ann, North Shore, Massachusetts, United States
This house rental in Rockport offers a yard, kitchen, parking, and space for 8, perfect for a family getaway with pets.
from $210
per night
Good(38 ratings)
from $210
per night
View deal
House Cape Ann
House ∙ 18 guests ∙ 10 bedrooms

Family-oriented house with yard, barbeque & hot tub | City view | Beach nearby | Good for workation

Cape Ann, North Shore, Massachusetts, United States
This Rockport house rental offers a hot tub, fireplace, and spacious yard, perfect for families and groups of up to 18 guests.
from $804
per night
Outstanding(44 ratings)
from $804
per night
View deal
Apartment Cape Ann
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with patio & BBQ | Nature view

Cape Ann, North Shore, Massachusetts, United States
This Gloucester apartment rental offers a kitchen and parking, perfect for a getaway with friends or family of up to four.
from $283
per night
Outstanding(39 ratings)
from $283
per night
View deal
House Cape Ann
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with grill

Cape Ann, North Shore, Massachusetts, United States
This Gloucester house rental features a kitchen, family-friendly spaces, and parking, perfect for a memorable getaway.
from $178
per night
Outstanding(27 ratings)
from $178
per night
View deal
House Cape Ann
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly vacation home with grill & terrace

Cape Ann, North Shore, Massachusetts, United States
This waterfront house rental in Gloucester features a kitchen and parking for six, perfect for a family getaway by the water.
from $591
per night
Outstanding(76 ratings)
from $591
per night
View deal
House Cape Ann
House ∙ 7 guests ∙ 2 bedrooms

Child-friendly house with patio & BBQ

Cape Ann, North Shore, Massachusetts, United States
from $407
per night
Outstanding(9 ratings)
from $407
per night
View deal
House Cape Ann
House ∙ 10 guests ∙ 5 bedrooms

Family-oriented house with garden, terrace & barbeque | 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 $431
per night
Outstanding(173 ratings)
from $431
per night
View deal
Apartment Cape Ann
Apartment ∙ 8 guests ∙ 3 bedrooms

Rental apartment with garden, barbecue & patio

Cape Ann, North Shore, Massachusetts, United States
This Gloucester apartment rental features a kitchen, yard, and parking, accommodating up to 8 guests for a perfect getaway.
from $359
per night
Outstanding(21 ratings)
from $359
per night
View deal

Vacation rentals and apartments with air conditioning

Cabin Cape Ann
from $191
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Fully equipped cottage with BBQ | Next to the beach

5.0
Outstanding(27 ratings)
Cape Ann, North Shore, Massachusetts, United States
Air conditioning
View deal
Apartment Cape Ann
from $171
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Child-friendly spacious holiday apartment with patio & grill

4.9
Outstanding(147 ratings)
Cape Ann, North Shore, Massachusetts, United States
Air conditioning
View deal
Apartment Cape Ann
from $280
per night
Apartment ∙ 8 guests ∙ 2 bedrooms

Holiday apartment with patio | Nature view

5.0
Outstanding(38 ratings)
Cape Ann, North Shore, Massachusetts, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

House Cape Ann
from $728
per night
House ∙ 8 guests ∙ 4 bedrooms

House with patio, pool & barbeque | Nature view

4.8
Outstanding(18 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony
View deal
House Cape Ann
from $629
per night
House ∙ 10 guests ∙ 4 bedrooms

House with BBQ & terrace

5.0
Outstanding(58 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony
View deal
House Cape Ann
from $519
per night
House ∙ 6 guests ∙ 3 bedrooms

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

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

Vacation Rentals With Fireplaces

Cabin Cape Ann
from $452
per night
Cabin ∙ 11 guests ∙ 5 bedrooms

Child-friendly cottage with barbecue & terrace | Next to the beach | Good for workation | Pet-friendly

4.9
Outstanding(11 ratings)
Cape Ann, North Shore, Massachusetts, United States
Fireplace
View deal
House Cape Ann
from $421
per night
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly vacation home with yard, barbecue & terrace | Nature view | Good for workation

5.0
Outstanding(159 ratings)
Cape Ann, North Shore, Massachusetts, United States
Fireplace
View deal
Apartment Cape Ann
from $167
per night
Apartment ∙ 5 guests ∙ 3 bedrooms

Rental apartment with patio, grill & yard | Good for workation

5.0
Outstanding(22 ratings)
Cape Ann, North Shore, Massachusetts, United States
Fireplace
View deal
See all offers

Budget-friendly rental options

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

Cabin Cape Ann
from $162
per night
Cabin ∙ 4 guests ∙ 1 bedroom

Fully equipped nice cottage with garden, barbecue & terrace | Beach nearby

4.9
Outstanding(138 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal
Cabin Cape Ann
from $192
per night
Cabin ∙ 3 guests ∙ 1 bedroom

Cottage with patio, grill & garden | Nature view

5.0
Outstanding(154 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal
Apartment Cape Ann
from $268
per night
Apartment ∙ 5 guests ∙ 3 bedrooms

Rental apartment with barbecue, yard & terrace

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

House Cape Ann
from $289
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with terrace, barbeque & hot tub | Nature view

4.9
Outstanding(77 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal
House Cape Ann
from $301
per night
House ∙ 6 guests ∙ 2 bedrooms

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

4.9
Outstanding(71 ratings)
Cape Ann, North Shore, Massachusetts, United States
View deal
Apartment Cape Ann
from $91
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Family-oriented nice rental apartment with barbecue & yard | Perfect for remote work

4.9
Outstanding(58 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. Nearly a quarter of the accommodations offer access to a pool. In addition, rentals with pools in Cape Ann have an average price of $447 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 736 rentals
💳 Possible discounts up to 25%
🌙 Nightly prices starting at $120
⭐ Popular amenities Pets allowed, Air conditioning and Internet
🐾 Pet friendly homes 108 homes
🏊 Vacation rentals with pools 179 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 $120 per night. $793 is the average nightly price for house rentals in Cape Ann. Apartment rentals in Cape Ann cost $397 per night on average.

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

There are 736 vacation homes from 11 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 179 vacation rentals available in Cape Ann for renting.

Are dogs allowed in vacation rentals in Cape Ann?

Sure, there are 108 vacation homes in Cape Ann that allow pets and the average cost is $635 per night.

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