Gloucester vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Gloucester
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Gloucester vacation rentals
Gloucester beach vacation rentals
Rental unit in Gloucester
Walk to Good Harbor Beach
Rental unit in Beverly
Garden City of the Northshore
Guest suite in Marblehead
Private Loft Right on Atlantic Avenue
Rental unit in Rockport
Harbor Retreat | Ocean View | Heart of Downtown
Cottage in Manchester-by-the-Sea
Singing Beach Cottage in Manchester by the Sea
Rental unit in Beverly
Entire 1st floor apt in charming seaside Beverly
Rental unit in Salem
Historic Salem Willows With Water View
Rental unit in Magnolia
Bright One Bedroom Apartment 5 Min Walk From Beach
Gloucester house rentals
Home in Gloucester
Wonderful Rocky Neck home on Gloucester harbor
Home in Gloucester
Gloucester Beach House, near Good Harbor Beach!
Home in Annisquam
June dates discounted!Overlooking Lobster Cove
Home in Rockport
Charming Toe-Hold, A Short Walk to Town and Beach
Home in Gloucester
Rocky Neck Retreat 4 Bedroom/2Bath/Kitchen/Laundry
Home in Marblehead
Bungalow in Downtown Marblehead
Home in Salisbury
Spacious 2 bedrooms waterfront free parking &Wi-fi
Home in Lynn
Clean, spacious In-Law Suite -Near Everything
Gloucester cottage rentals
Cottage in Rockport
Periwinkle Cottage #1 -walk to everything!
Cottage in Gloucester
SeaHaven Cottage at Stage Fort Park
Cottage in Kittery Point
Cozy Maine Cottage by the Sea
Cottage in Rockport
Retreat in the Trees close to beaches
Cottage in Gloucester
Bright & Cheerful 3BR+den, Gloucester Cottage
Cottage in Hampton Beach
Cozy Cottage steps from Hampton Strip With Parking
Cottage in Newbury
Sunset Bliss a Plum Island Oasis- Beach 3 min walk
Cottage in Newburyport
Plum Island’s TRUE NORTH COTTAGE
Quick stats about vacation rentals in Gloucester
Total rentals
540 properties
Rentals with dedicated workspaces
250 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
130 properties allow pets
Family-friendly rentals
340 properties are a good fit for families
Total number of reviews
22K reviews
Frequently Asked Questions
What types of vacation rentals are available in Gloucester?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Gloucester. From over 240 house rentals to over 40 cottage rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Where should I stay in Gloucester?
Make yourself at home in Gloucester by choosing from our most frequently booked neighborhoods. We have over 230 vacation rentals in West Gloucester, and over 310 vacation rentals in Annisquam.
Are there vacation rentals with a dedicated workspace in Gloucester?
Yes! Work meets play with ease at over 250 vacation rentals in Gloucester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Gloucester?
Four-legged friends are welcome in Gloucester. Choose from more than 130 vacation rentals for guests traveling with pets.
Are there Gloucester vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Gloucester, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in cottage rentals in Gloucester?
Experience the best of Gloucester with our cottage rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Gloucester have a gym?
Absolutely! We offer over 10 house rentals with a gym in Gloucester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Gloucester have self check-in?
Absolutely! We offer over 100 house rentals with self check-in in Gloucester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Gloucester have a bbq area?
Absolutely! We offer over 110 house rentals with a bbq area in Gloucester. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Gloucester?
Gloucester has more than 210 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Destinations to explore
- Cape Cod Vacation rentals
- Martha's Vineyard Vacation rentals
- Cambridge Vacation rentals
- Portland Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Québec City Vacation rentals
- Québec Vacation rentals
- Rentals with a fireplace Gloucester
- Apartment rentals Gloucester
- Pet-friendly rentals Gloucester
- Condo rentals Gloucester
- Rentals with breakfast Gloucester
- Beach house rentals Gloucester
- Monthly Rentals Gloucester
- Beachfront rentals Gloucester
- Kid-friendly rentals Gloucester
- Rentals with a fire pit Gloucester
- Rentals with beach access Gloucester
- House rentals Gloucester
- Rentals with outdoor seating Gloucester
- Rentals with a patio Gloucester
- Waterfront rentals Gloucester
- Rentals with an EV charger Gloucester
- Rentals with a washer and dryer Gloucester
- Private suite rentals Gloucester
- Family-friendly rentals Gloucester
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes