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
Tiny home in Rockport
4.94 out of 5 average rating, 129 reviewsLittle Red House on Bearskin Neck!
Apartment in Rockport
4.96 out of 5 average rating, 259 reviewsHarbor Retreat | Ocean View | Heart of Downtown
Home in Gloucester
4.99 out of 5 average rating, 157 reviewsRocky Neck Retreat 4 Bedroom/2Bath/Kitchen/Laundry
Apartment in Beverly
4.92 out of 5 average rating, 453 reviewsPrivate apartment 10 min to Salem!
Apartment in Gloucester
4.85 out of 5 average rating, 105 reviewsBright One Bedroom Apartment 5 Min Walk From Beach
Apartment in Beverly
4.97 out of 5 average rating, 185 reviewsGarden City of the Northshore
Apartment in Rockport
4.79 out of 5 average rating, 172 reviewsRockport's Best Kept Secret: 2 Bed/1 Bath on Bears
Guest suite in Gloucester
4.98 out of 5 average rating, 128 reviewsThe Carriage House near Plum Cove Beach
Gloucester house rentals
Home in Gloucester
4.96 out of 5 average rating, 121 reviewsBooking spring/summer-Overlooking Lobster Cove
Home in Gloucester
4.82 out of 5 average rating, 162 reviewsGloucester Private Contemporary 4 bedrooms
Home in Gloucester
4.91 out of 5 average rating, 107 reviewsGloucester Beach House, near Good Harbor Beach!
Home in Marblehead
4.91 out of 5 average rating, 174 reviewsBungalow in Downtown Marblehead
Home in Gloucester
4.8 out of 5 average rating, 137 reviewsGloucester getaway ocean escape
Home in Kittery
4.95 out of 5 average rating, 436 reviewswater view property "The Little House"
Home in Rye
4.99 out of 5 average rating, 228 reviews*Beachfront* Vintage Coastal Cottage - Relaxation
Home in Lynn
4.91 out of 5 average rating, 228 reviewsClean, spacious In-Law Suite -Near Everything
Beach house rentals in Gloucester
Home in Marblehead
4.98 out of 5 average rating, 188 reviewsAuthentic Rustic Single Family Home in Old Town
Home in Salisbury
4.87 out of 5 average rating, 163 reviewsSpacious 2 bedrooms waterfront free parking &Wi-fi
Home in Revere
4.78 out of 5 average rating, 144 reviewsRenovated Cozy City Getaway
Home in Marblehead
4.88 out of 5 average rating, 137 reviewsModern 4 Bed 2 Bath home W/ Private outdoor space
Home in Marblehead
4.9 out of 5 average rating, 175 reviewsCharming 4 Bedroom House on Pond + Walk to Sea!
Home in Beverly
4.84 out of 5 average rating, 146 reviewsBeverly Beach House- Upper Deck
Home in Salem
5.0 out of 5 average rating, 131 reviewsDowntown Salem Home-Free Parking-Ferry to Boston
Home in Newbury
4.9 out of 5 average rating, 102 reviewsBrivera by the Sea, a Beautiful Plum Island Escape
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 condo rentals in Gloucester?
Experience the best of Gloucester with our condo rentals, starting at about $80 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 10 homes with a gym, over 110 homes with a bbq area, over 100 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.
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