Skip to content

Cape Ann vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Cape Ann

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

SUPERHOST
Rental unit in Rockport
Cozy Waterfront Suite in Dock Square + Parking!
Charming waterfront suite, with rare onsite parking and private entrance in the heart of Rockport. Views and access to harbor and ocean from the back yard. Beaches, galleries, restaurants, coffee shops, live music and shopping on Bearskin Neck just steps away. This recently updated suite has a complete kitchen, sitting area with TV, bedroom and bathroom, with small shower. The kitchen has a fridge, stove, oven, microwave, Keurig and table for two. Cozy and comfortable with all amenities.
$229 per night
SUPERHOST
Rental unit in Rockport
1BR|Private Deck with Ocean Views|King Bed|Parking
• Newly remodeled and professionally furnished space! • Steps to Beaches, Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu • Private off street parking spot for 2 cars • High Speed Wi-Fi and AC throughout • 10 minute walk from commuter rail to Boston • Smart TV equipped to stream all your favorites • Fully stocked and renovated kitchen • 2 levels with plenty of space • Comfortable KING size memory foam bed • Convenient EV charging right across the street!
$160 per night
SUPERHOST
Rental unit in Rockport
The Bookstore|2 Private Parking Spots|2 King Beds
• Newly furnished and professionally designed space! • Steps to Front Beach, Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu Performance Center. • Private off street parking spot for 2 cars • High Speed Wi-Fi and 4K Smart TV • 10 minute walk from commuter rail to Boston • Smart TV equipped to stream all your favorites • Fully stocked and renovated kitchen • 2 Comfortable KING size memory foam beds • Convenient EV charging right across the street!
$201 per night

Cape Ann beach vacation rentals

SUPERHOST
Condo in Rockport
Dream waterfront town center 1 bedroom apartment
$220 per night
SUPERHOST
Rental unit in Rockport
"Rockport Sail Loft: 2 Bed/1 Bath Oceanfront Haven
$184 per night
SUPERHOST
Guest suite in Gloucester
Sunsets at the Seawall - A Coastal Hideaway
$150 per night
SUPERHOST
Rental unit in Rockport
Ocean View unit with Private Roofdeck in Rockport
$232 per night

Cape Ann cottage rentals

SUPERHOST
Cottage in Rockport
Quaint Oceanfront Cottage in Rockport MA
$150 per night
SUPERHOST
Cottage in Rockport
Retreat in the Trees close to Salem witches
$245 per night
SUPERHOST
Cottage in Gloucester
Sunny & private cottage: Discounts for Off-Season
$265 per night
SUPERHOST
Cottage in Gloucester
Robyn's Cottage at Plum Cove
$246 per night

Cape Ann house rentals

SUPERHOST
Home in Rockport
NEW 2BR Home|Minutes to Downtown Rockport+Beach
$212 per night
SUPERHOST
Home in Gloucester
Water views! Booking fall/holidays now
$239 per night
SUPERHOST
Home in Rockport
Cozy & Quaint 2 Bedroom
$169 per night
SUPERHOST
Private room in Gloucester
Room 1: The Lavender room at the Beach Rose
$177 per night

Other types of stays on Airbnb

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Essex County
  5. Rockport
  6. Cape Ann