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
Apartment in Gloucester
4.94 out of 5 average rating, 110 reviewsWalk to Good Harbor Beach
Guesthouse in Rockport
5.0 out of 5 average rating, 218 reviewsSea Mist Cottage Rockport, MA
Tiny home in Rockport
4.94 out of 5 average rating, 129 reviewsLittle Red House on Bearskin Neck!
Guest suite in Gloucester
4.98 out of 5 average rating, 128 reviewsThe Carriage House near Plum Cove Beach
Home in Gloucester
4.99 out of 5 average rating, 158 reviewsRocky Neck Retreat 4 Bedroom/2Bath/Kitchen/Laundry
Apartment in Beverly
4.92 out of 5 average rating, 454 reviewsPrivate apartment 10 min to Salem!
Apartment in Beverly
4.94 out of 5 average rating, 625 reviewsBeverly Farms Apartment “Homeport”
Apartment in Beverly
4.96 out of 5 average rating, 187 reviewsGarden City of the Northshore
Gloucester house rentals
Home in Rockport
4.97 out of 5 average rating, 283 reviewsCharming Toe-Hold, A Short Walk to Town and Beach
Home in Gloucester
4.82 out of 5 average rating, 163 reviewsGloucester Private Contemporary 4 bedrooms
Home in Marblehead
4.91 out of 5 average rating, 174 reviewsBungalow in Downtown Marblehead
Home in Kittery
4.95 out of 5 average rating, 437 reviewswater view property "The Little House"
Home in Lynn
4.91 out of 5 average rating, 228 reviewsClean, spacious In-Law Suite -Near Everything
Home in Gloucester
4.8 out of 5 average rating, 137 reviewsGloucester getaway ocean escape
Home in Ipswich
4.98 out of 5 average rating, 170 reviewsStagehill Beach House
Home in Rye
4.99 out of 5 average rating, 230 reviews*Beachfront* Vintage Coastal Cottage - Relaxation
Gloucester cottage rentals
Cottage in Rockport
4.98 out of 5 average rating, 101 reviewsPeriwinkle Cottage #1 -walk to everything!
Cottage in Gloucester
4.86 out of 5 average rating, 157 reviewsBright & Cheerful 3BR+den, Gloucester Cottage
Cottage in Gloucester
4.85 out of 5 average rating, 157 reviewsSeaHaven Cottage at Stage Fort Park
Cottage in Rye
4.91 out of 5 average rating, 120 reviewsSeacoast Solo
Cottage in Rockport
4.8 out of 5 average rating, 100 reviewsRetreat in the Trees close to beaches
Cottage in Newburyport
5.0 out of 5 average rating, 145 reviewsPlum Island’s TRUE NORTH COTTAGE
Cottage in Newbury
4.82 out of 5 average rating, 101 reviewsSunset Bliss a Plum Island Oasis- Beach 3 min walk
Cottage in Epsom
4.97 out of 5 average rating, 191 reviewsSmokey Pines Camp
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
Where should I stay in Gloucester?
Make yourself at home in Gloucester by choosing from our most frequently booked neighborhoods. We have over 310 vacation rentals in Annisquam, and over 230 vacation rentals in West Gloucester.
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.
What are the most popular amenities for House Rentals in Gloucester?
Enhance your stay in our House Rentals with the most popular amenities: over 110 homes with a bbq area, over 10 homes with a gym, over 100 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.
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