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.

Guest favorite
Home in Gloucester
Rocky Neck Retreat 4 Bedroom/2Bath/Kitchen/Laundry
.Relaxing private location .4 beds 2 baths with full kitchen/pans/Dishwasher/Wash/Dryer.Renovated organic design integrates historic architecture with modern touches.If you come for hikes, beach/music/food scene, you will enjoy the Rocky Neck District .The unique home has 4 bedrooms /4 Queen Beds. Speedy WIFI .Parking is up a steep narrow drive . NO trucks or Large SUVs. 2 cars max. Note* Kitchen and LR are upstairs.There are stairs. Contact owner for questions re:parking or limited mobility.
Aug 24 – 31
$459 per night
4.99 out of 5 average rating, 153 reviews
Guest favorite
Home in Gloucester
Booking spring/summer-Overlooking Lobster Cove
Booking spring, summer and fall 2024 now. Water views/access, sunsets above Lobster Cove on Washington St. Ideal for couple, NEW KING BED in master, queen in 2nd. Fast WiFi./TV. Not suitable for young children. Central A/C. 2nd fl unit large windows. Open living/dining/kitchen area . 2 queen BR w new mattresses, sound machines, individual AC/heat. Overlooks beautiful Lobster Cove and footbridge. Minutes walk to the village of Annisquam and Lighthouse Beach. Small deck. Swim/kayak out your door.
Nov 10 – 17
$265 per night
4.96 out of 5 average rating, 121 reviews
Guest favorite
Loft in Rockport
Chic Downtown Loft ☆ Private Parking ☆ Ocean View
Enjoy the coastal and seaside views from the renovated and bright "jewel" located in the charming seaside New England town of Rockport on Cape Ann. The loft is centrally located is literally steps to the beaches, the Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu. 1-min walk to Bearskin Neck & Motif No.1 5-min walk to Front Beach + easy access to many others 8-min drive to Halibut Point Park 25-min drive to Salem 1-hour drive to Boston 15-min walk MBTA Train Station
Nov 29 – Dec 6
$137 per night
5.0 out of 5 average rating, 192 reviews

Popular amenities for Gloucester vacation rentals

Stay near Gloucester's top sights

Cape Ann Whale Watch41 locals recommend
Beauport Hotel Gloucester35 locals recommend
7 Seas Whale Watch19 locals recommend
Stage Fort Park and Beach45 locals recommend
Causeway Restaurant41 locals recommend
Seaport Grill31 locals recommend

Gloucester beach vacation rentals

Guest favorite
Condo in Rockport
6 Tuna Wharf - Harbor right outside kitchen door!
Jun 7 – 14
$299 per night
4.99 out of 5 average rating, 184 reviews
Guest favorite
Apartment in Gloucester
Walk to Good Harbor Beach
Sep 2 – 9
$175 per night
4.94 out of 5 average rating, 108 reviews
Superhost
Home in Gloucester
Gloucester Beach House, near Good Harbor Beach!
Mar 31 – Apr 7
$169 per night
4.9 out of 5 average rating, 104 reviews
Guest favorite
Guesthouse in Rockport
Sea Mist Cottage Rockport, MA
Sep 18 – 25
$194 per night
5.0 out of 5 average rating, 214 reviews
Guest favorite
Guest suite in Rockport
Charming Studio in the Pines
Oct 25 – Nov 1
$104 per night
4.87 out of 5 average rating, 197 reviews
Guest favorite
Apartment in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
Oct 9 – 16
$349 per night
4.78 out of 5 average rating, 200 reviews
Guest favorite
Apartment in Rockport
Mary's By The Sea
Sep 20 – 27
$167 per night
4.94 out of 5 average rating, 148 reviews
Guest favorite
Townhouse in Gloucester
Between 2 Beaches
Jan 14 – 21
$488 per night
5.0 out of 5 average rating, 150 reviews
Guest favorite
Tiny home in Rockport
Little Red House on Bearskin Neck!
Jun 14 – 21
$180 per night
4.94 out of 5 average rating, 128 reviews
Guest favorite
Cottage in Manchester-by-the-Sea
Singing Beach Cottage in Manchester by the Sea
Aug 16 – 23
$215 per night
4.95 out of 5 average rating, 337 reviews
Guest favorite
Cottage in Gloucester
SeaHaven Cottage at Stage Fort Park
Apr 25 – May 2
$350 per night
4.85 out of 5 average rating, 157 reviews
Guest favorite
Apartment in Rockport
Old Harbor
Feb 22 – Mar 1
$293 per night
4.91 out of 5 average rating, 117 reviews

Gloucester house rentals

Guest favorite
Home in Beverly
Historic New England Arts & Crafts home
Jul 28 – Aug 4
$359 per night
4.91 out of 5 average rating, 116 reviews
Guest favorite
Home in Salisbury
Spacious 2 bedrooms waterfront free parking &Wi-fi
Oct 4 – 11
$134 per night
4.86 out of 5 average rating, 157 reviews
Guest favorite
Home in Salisbury
NEW 3BR home, incredible views - Beach across St
Apr 14 – 21
$201 per night
4.91 out of 5 average rating, 113 reviews
Guest favorite
Home in Marblehead
Modern 4 Bed 2 Bath home W/ Private outdoor space
Dec 14 – 21
$255 per night
4.88 out of 5 average rating, 128 reviews
Guest favorite
Home in Rye
*Beachfront* Vintage Coastal Cottage - Relaxation
Jan 23 – 30
$196 per night
4.99 out of 5 average rating, 215 reviews
Guest favorite
Home in Marblehead
Bungalow in Downtown Marblehead
Nov 16 – 23
$125 per night
4.91 out of 5 average rating, 167 reviews
Guest favorite
Home in North Andover
Nana-tucket Inn
Apr 19 – 26
$750 per night
4.94 out of 5 average rating, 127 reviews
Guest favorite
Home in Marblehead
Authentic Rustic Single Family Home in Old Town
Feb 16 – 23
$270 per night
4.98 out of 5 average rating, 185 reviews
Guest favorite
Home in Lynn
Clean, spacious In-Law Suite -Near Everything
Dec 4 – 11
$127 per night
4.91 out of 5 average rating, 225 reviews
Guest favorite
Home in Gloucester
Gloucester Beach House
Jun 16 – 23
$205 per night
4.94 out of 5 average rating, 17 reviews
Guest favorite
Home in Gloucester
Harbor View Walk to Town&Beach, 6 Guests King beds
Apr 15 – 22
$236 per night
4.97 out of 5 average rating, 97 reviews
Guest favorite
Home in Gloucester
Seaside Home Minutes to Rockport and Gloucester!
Apr 26 – May 3
$142 per night
4.93 out of 5 average rating, 55 reviews

Gloucester cottage rentals

Guest favorite
Cottage in Essex
French Flair "Pied a Terre" Cottage on the Marsh
May 10 – 17
$175 per night
4.97 out of 5 average rating, 212 reviews
Guest favorite
Cottage in Rockport
Periwinkle Cottage #1 -walk to everything!
Mar 26 – Apr 2
$164 per night
4.98 out of 5 average rating, 100 reviews
Guest favorite
Cottage in Gloucester
Bright & Cheerful 3BR+den, Gloucester Cottage
Apr 19 – 26
$329 per night
4.86 out of 5 average rating, 157 reviews
Guest favorite
Cottage in Newbury
Sunset Bliss a Plum Island Oasis- Beach 3 min walk
Jun 15 – 22
$462 per night
4.82 out of 5 average rating, 101 reviews
Guest favorite
Cottage in Newburyport
Plum Island’s TRUE NORTH COTTAGE
Feb 25 – Mar 4
$625 per night
5.0 out of 5 average rating, 144 reviews
Guest favorite
Cottage in Rye
Seacoast Solo
Jun 20 – 27
$90 per night
4.91 out of 5 average rating, 120 reviews
Guest favorite
Cottage in Kittery
Cozy Maine Cottage by the Sea
Oct 27 – Nov 3
$147 per night
4.95 out of 5 average rating, 139 reviews
Guest favorite
Cottage in Kittery
Charming Coastal Maine Cottage
May 14 – 21
$225 per night
4.96 out of 5 average rating, 271 reviews
Guest favorite
Cottage in Salem
Authentic 1739 Two Bdrm House in Salem
Mar 19 – 26
$253 per night
4.97 out of 5 average rating, 137 reviews
Guest favorite
Cottage in Hampton
2 Bedroom Beach Bungalow, Steps from the Beach!
Oct 25 – Nov 1
$211 per night
4.95 out of 5 average rating, 216 reviews
Guest favorite
Cottage in Hampton
The 1907 on Nudd: Sleeps 8 | Front Porch | Parking
Apr 8 – 15
$272 per night
4.89 out of 5 average rating, 103 reviews
Guest favorite
Cottage in Kittery
Badgers Island Cottage
Jan 2 – 9
$212 per night
4.94 out of 5 average rating, 124 reviews

Quick stats about vacation rentals in Gloucester

Total rentals

530 properties

Rentals with dedicated workspaces

240 properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

130 properties allow pets

Family-friendly rentals

320 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 40 cottage rentals to over 230 house 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 220 vacation rentals in West Gloucester, and over 300 vacation rentals in Annisquam.

  • Are there vacation rentals with a dedicated workspace in Gloucester?

    Yes! Work meets play with ease at over 240 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 $120 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 200 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Essex County
  5. Gloucester