Airbnb, Vacation Rentals in Gloucester, MA

Compare 944 available beachfront holiday vacation rentals, starts from $39

Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Find the best vacation rental

ACCOMMODATION TYPES

Save Up To 79%

Airbnb, Vacation rentals and hotel deals in Gloucester, MA

Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!
9.6 (17 reviews)
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!
Holiday home · 2 Guests · 1 Bedroom
$189 /night*
View deal
Extended Stay America Suites - Boston - Peabody
Extended Stay America Suites - Boston - Peabody
Extended Stay America Suites - Boston - Peabody
Extended Stay America Suites - Boston - Peabody
6.7 (219 reviews)
Extended Stay America Suites - Boston - Peabody
Hotel · 2 Guests · 1 Bedroom
$136 /night
View deal
Beauport Hotel Gloucester
Beauport Hotel Gloucester
Beauport Hotel Gloucester
Beauport Hotel Gloucester
9.5 (301 reviews)
Beauport Hotel Gloucester
Hotel · 2 Guests · 1 Bedroom
$224 /night
View deal
Harborview Inn
Harborview Inn
Harborview Inn
Harborview Inn
9.3 (93 reviews)
Harborview Inn
Inn · 2 Guests · 1 Bedroom
$189 /night
View deal
Salem Waterfront Hotel & Suites
Salem Waterfront Hotel & Suites
Salem Waterfront Hotel & Suites
Salem Waterfront Hotel & Suites
8.8 (640 reviews)
Salem Waterfront Hotel & Suites
Hotel · 2 Guests · 1 Bedroom
$156 /night
View deal
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
9.8 (150 reviews)
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Apartment · 2 Guests · 1 Bedroom
$175 /night*
View deal
Compass Rose Inn
Compass Rose Inn
Compass Rose Inn
Compass Rose Inn
9.6 (51 reviews)
Compass Rose Inn
Inn · 2 Guests · 1 Bedroom
$219 /night
View deal
Best Western Plus North Shore Hotel
Best Western Plus North Shore Hotel
Best Western Plus North Shore Hotel
Best Western Plus North Shore Hotel
8.7 (601 reviews)
Best Western Plus North Shore Hotel
Hotel · 2 Guests · 1 Bedroom
$104 /night
View deal
HALLOWEEN SEASON! STUNNING OCEANFRONT HOUSE NEAR SALEM.
HALLOWEEN SEASON! STUNNING OCEANFRONT HOUSE NEAR SALEM.
HALLOWEEN SEASON! STUNNING OCEANFRONT HOUSE NEAR SALEM.
HALLOWEEN SEASON! STUNNING OCEANFRONT HOUSE NEAR SALEM.
9.6 (9 reviews)
HALLOWEEN SEASON! STUNNING OCEANFRONT HOUSE NEAR SALEM.
Holiday home · 2 Guests · 1 Bedroom
$125 /night*
View deal
Knight's Inn Boston/Danvers
Knight's Inn Boston/Danvers
Knight's Inn Boston/Danvers
Knight's Inn Boston/Danvers
6.2 (384 reviews)
Knight's Inn Boston/Danvers
Hotel · 2 Guests · 1 Bedroom
$159 /night
View deal
Sonesta Select Boston Danvers
Sonesta Select Boston Danvers
Sonesta Select Boston Danvers
Sonesta Select Boston Danvers
8.5 (288 reviews)
Sonesta Select Boston Danvers
Hotel · 2 Guests · 1 Bedroom
$108 /night
View deal
Essex Street Inn & Suites, Ascend Hotel Collection
Essex Street Inn & Suites, Ascend Hotel Collection
Essex Street Inn & Suites, Ascend Hotel Collection
Essex Street Inn & Suites, Ascend Hotel Collection
9.3 (217 reviews)
Essex Street Inn & Suites, Ascend Hotel Collection
Hotel · 2 Guests · 1 Bedroom
$176 /night
View deal
Gloucester Whale Watch Tour! Comfortable Unit, Pet-friendly Property!
Gloucester Whale Watch Tour! Comfortable Unit, Pet-friendly Property!
Gloucester Whale Watch Tour! Comfortable Unit, Pet-friendly Property!
Gloucester Whale Watch Tour! Comfortable Unit, Pet-friendly Property!
10 (1 review)
Gloucester Whale Watch Tour! Comfortable Unit, Pet-friendly Property!
Holiday home · 2 Guests · 1 Bedroom
$138 /night*
View deal
A tranquil ocean retreat steps from the water's edge
A tranquil ocean retreat steps from the water's edge
A tranquil ocean retreat steps from the water's edge
A tranquil ocean retreat steps from the water's edge
10 (86 reviews)
A tranquil ocean retreat steps from the water's edge
Apartment · 2 Guests · 1 Bedroom
$175 /night*
View deal
Hampton Inn Salem, Ma
Hampton Inn Salem, Ma
Hampton Inn Salem, Ma
Hampton Inn Salem, Ma
9.2 (368 reviews)
Hampton Inn Salem, Ma
Hotel · 2 Guests · 1 Bedroom
$148 /night
View deal
The Wylie Inn and Conference Center at Endicott College
The Wylie Inn and Conference Center at Endicott College
The Wylie Inn and Conference Center at Endicott College
The Wylie Inn and Conference Center at Endicott College
8.7 (391 reviews)
The Wylie Inn and Conference Center at Endicott College
Hotel · 2 Guests · 1 Bedroom
$135 /night
View deal
Candlewood Suites Boston North Shore Danvers, an IHG Hotel
Candlewood Suites Boston North Shore Danvers, an IHG Hotel
Candlewood Suites Boston North Shore Danvers, an IHG Hotel
Candlewood Suites Boston North Shore Danvers, an IHG Hotel
8.4 (951 reviews)
Candlewood Suites Boston North Shore Danvers, an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$113 /night
View deal
#Weddings #Holidays #Corporate short term ? Just need some “in between” place ?
#Weddings #Holidays #Corporate short term ? Just need some “in between” place ?
#Weddings #Holidays #Corporate short term ? Just need some “in between” place ?
#Weddings #Holidays #Corporate short term ? Just need some “in between” place ?
10 (5 reviews)
#Weddings #Holidays #Corporate short term ? Just need some “in between” place ?
Apartment · 2 Guests · 1 Bedroom
$200 /night*
View deal
Riverview charming apt near beach
Riverview charming apt near beach
Riverview charming apt near beach
Riverview charming apt near beach
9.4 (6 reviews)
Riverview charming apt near beach
Apartment · 2 Guests · 1 Bedroom
$165 /night*
View deal
The Salem Inn
The Salem Inn
The Salem Inn
The Salem Inn
9.0 (348 reviews)
The Salem Inn
Inn · 2 Guests · 1 Bedroom
$209 /night
View deal
Search all

Vacation Destinations Near Gloucester, MA

Airbnb, Holiday Beachfront House with Air Conditioning in Gloucester, MA

Sally Webster Inn
Sally Webster Inn
Sally Webster Inn
Sally Webster Inn
Air Conditioning
9.6 (17 reviews)
Sally Webster Inn
B & B · 2 Guests · 1 Bedroom
$216 /night
View deal
Search all
What Are The Well Liked Rental Amenities in Gloucester, MA?
Gloucester, MA Rental Amenities
+
There are in total of 15 rental amenities in Gloucester, shown above with the property numbers. In Gloucester, 458 rentals offer Internet or Wifi, 445 rentals offer TV, 420 rentals offer Parking Available. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Pool, Hot Tub.
How Does The Vacation Home Rental Price Look Like in Gloucester, MA?
Vacation Rentals Price Information in Gloucester, MA
+
The graph shows the percentages of vacation homes in each price bucket. Gloucester has the largest percentage (16.45%) of homes in $150 - $200 price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
Which Accommodations Should I Pick in Gloucester, MA?
Vacation Rental Property Types in Gloucester, MA
+
Before visiting Gloucester, it is a good idea to explore all the accommodation types in this area, and pick the one that fits your group well. All the available accommodation types are: House, Cottage, Apartment, Condo, Townhome, Studio, Guest House, Estate, Hotel, Villa, Chateau / Country House, Bungalow, Farmhouse, Barn. House is the most-liked rental type, with the largest percentage of 53.81%. The biggest home in this area available for rent is around 11840 square feet.The least popular accommodation in Gloucester is Barn rentals
How Many Accommodations Are Not Pets Friendly in Gloucester, MA?
Pets Allowed vs Not Allowed in Gloucester, MA
+
27.12% of vacation homes in Gloucester are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
Trail Recommendations in Gloucester, MA Area?
Best Trails In Gloucester, MA
+
The most visited trails here in Gloucester are: Gloucester Biking Loop, Stage Fort Trail, Dogtown Loop Trail to Briar Swamp, Babson Reservoir Dogtown Loop Trail, Good Harbor Beach, Goose Cove Reservoir, Long Beach, Gloucester Breakwater, Ravenswood Park Trail, Annisquam Lighthouse.
Where Are The Campgrounds in Gloucester, MA Area?
Most Visited Campgrounds In Gloucester, MA
+
The best RV campgrounds here in Gloucester are: Old Stage Campground, Barrington Shores Campground, Winter Island Park Campground, Harold Parker Campground, Salisbury Beach State Reservation Campground, Cascara Campground, Wompatuck Campground, Tidewater Campground, Wakeda Campground, Green Gate Campground.
Which Airports Should I Choose To Get To Gloucester, MA?
Suggested Airports in Gloucester, MA
+

Other Vacation Rentals Ideas

Airbnb, Holiday Beachfront House with Full Kitchen, and Other Rental Options in Gloucester, MA

Make Every Trip Halloween-thy
Make Every Trip Halloween-thy
Make Every Trip Halloween-thy
Make Every Trip Halloween-thy
Full Kitchen
7.0 (2 reviews)
Make Every Trip Halloween-thy
Holiday home · 2 Guests · 1 Bedroom
$550 /night*
View deal
*NEW Spooky 2BR|Downtown Salem|Beach|Parking
*NEW Spooky 2BR|Downtown Salem|Beach|Parking
*NEW Spooky 2BR|Downtown Salem|Beach|Parking
*NEW Spooky 2BR|Downtown Salem|Beach|Parking
Full Kitchen
9.8 (9 reviews)
*NEW Spooky 2BR|Downtown Salem|Beach|Parking
Holiday home · 2 Guests · 1 Bedroom
$137 /night*
View deal
Sailors Rest: Fabulous Yard, Near Beach, Town, & Bike Trail, Superbox & Smart TV, Fast WiFi
Sailors Rest: Fabulous Yard, Near Beach, Town, & Bike Trail, Superbox & Smart TV, Fast WiFi
Sailors Rest: Fabulous Yard, Near Beach, Town, & Bike Trail, Superbox & Smart TV, Fast WiFi
Sailors Rest: Fabulous Yard, Near Beach, Town, & Bike Trail, Superbox & Smart TV, Fast WiFi
Full Kitchen
9.8 (7 reviews)
Sailors Rest: Fabulous Yard, Near Beach, Town, & Bike Trail, Superbox & Smart TV, Fast WiFi
Holiday home · 2 Guests · 1 Bedroom
$157 /night*
View deal
Search all

Airbnb, Vacation Rentals, Cottage with Fireplace, and Other Rental Options in Gloucester, MA

Plum Island - Charming 2 BR Cottage by the Sea
Plum Island - Charming 2 BR Cottage by the Sea
Plum Island - Charming 2 BR Cottage by the Sea
Plum Island - Charming 2 BR Cottage by the Sea
Fireplace
10 (69 reviews)
Plum Island - Charming 2 BR Cottage by the Sea
Cottage · 2 Guests · 1 Bedroom
$250 /night*
View deal
Grab the last open summer week! 9/2-9/9 is open!
Grab the last open summer week! 9/2-9/9 is open!
Grab the last open summer week! 9/2-9/9 is open!
Grab the last open summer week! 9/2-9/9 is open!
Fireplace
Grab the last open summer week! 9/2-9/9 is open!
Cottage · 2 Guests · 1 Bedroom
$270 /night*
View deal
Search all
* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
See all offers