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Gloucester vacation rentals

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Top-rated vacation rentals in Gloucester

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
Welcome 2023! This is Gloucesters' 400th Anniversary! You will be sure to enjoy various special activities and events this summer.( Check Gloucester 400-) We are located in the "quiet end", on a private residential dead end street in the historic artist colony of Rocky Neck. Nearby public transportation, including Audubon, cultural events and the Gloucester Stage Company. Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV
Dec 27 – Jan 3
$106 per night
Superhost
Home in Gloucester
Wonderful Rocky Neck home on Gloucester harbor
2 Bedroom with Loft, 1 Bathroom fully furnished Home on Gloucester harbor. Dead end street with 3 off street parking spots. Restaurants, local art gallery's, the beach all just a short walk away. Wake up with the sweet smell of ocean air and the sound of seagulls calling. Enjoy your breakfast with a million dollar view on the 4 season porch with 8 sliding windows overlooking the harbor. You could spend hours watching the boats go by as you read a good book with your fur baby on your lap.
Apr 2 – 9
$333 per night
Guest favorite
Guest suite in Gloucester
SplashLanding Private Beach Getaway in Gloucester
Jan-March 2024 open for monthly rentals. Must Book Summer 2024 via Airbnb website not the APP! *Our 2nd unit SquishInn has openings beginning April 2024 airbnb.com/h/squishinn-gloucester-ma Long walks on a private beach. Get sun-kissed; toes in the sand. Romantic dinners on the deck. Cozy in Winter (Energy Star home and Radiant heat throughout). TRAVELING WITH ANOTHER COUPLE? Book Private Beach Getaway SquishInn. Our 2nd unit for adult couples. Now another 2 friends can join you!
Jul 8 – 15
$322 per night

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
Home in Gloucester
Booking spring/summer-Overlooking Lobster Cove
May 15 – 22
$265 per night
Guest favorite
Cottage in Manchester-by-the-Sea
Singing Beach Cottage in Manchester by the Sea
Jun 20 – 27
$114 per night
Guest favorite
Home in Gloucester
Rocky Neck Retreat 4 Bedroom/2Bath/Kitchen/Laundry
Sep 13 – 20
$469 per night
Guest favorite
Condo in Rockport
Bearskin Neck Rockport ★ Amazing Views ★ Parking
Apr 26 – May 3
$261 per night
Guest favorite
Townhouse in Gloucester
Between 2 Beaches
Nov 9 – 16
$457 per night
Guest favorite
Apartment in Gloucester
Bright One Bedroom Apartment 5 Min Walk From Beach
Sep 1 – 8
$212 per night
Guest favorite
Guest suite in Gloucester
The Carriage House near Plum Cove Beach
Oct 13 – 20
$225 per night
Guest favorite
Loft in Rockport
Loft Apartment With Ocean Views
Jun 13 – 20
$243 per night
Guest favorite
Apartment in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
Oct 24 – 31
$392 per night
Guest favorite
Apartment in Gloucester
Walk to Good Harbor Beach
Mar 28 – Apr 4
$175 per night
Guest favorite
Condo in Rockport
6 Tuna Wharf - Harbor right outside kitchen door!
Jun 30 – Jul 7
$318 per night
Guest favorite
Apartment in Rockport
1 Bedroom Apartment By Harbor - Centrally Located
Jan 7 – 14
$134 per night

Gloucester house rentals

Guest favorite
Home in Gloucester
Gloucester Private Contemporary 4 bedrooms
May 20 – 27
$336 per night
Guest favorite
Home in Rockport
Charming Toe-Hold, A Short Walk to Town and Beach
Dec 1 – 8
$204 per night
Guest favorite
Home in Ipswich
Stagehill Beach House
Apr 28 – May 5
$462 per night
Superhost
Home in Gloucester
Gloucester getaway ocean escape
Oct 27 – Nov 3
$248 per night
Guest favorite
Home in Rye
*Beachfront* Vintage Coastal Cottage - Relaxation
Dec 10 – 17
$221 per night
Guest favorite
Home in Beverly
Historic New England Arts & Crafts home
Jul 17 – 24
$359 per night
Guest favorite
Home in Salisbury
NEW 3BR home, incredible views - Beach across St
Mar 5 – 12
$182 per night
Guest favorite
Home in North Andover
Nana-tucket Inn
Apr 12 – 19
$750 per night
Guest favorite
Home in Marblehead
Bungalow in Downtown Marblehead
Feb 10 – 17
$125 per night
Guest favorite
Home in Northwood
Pleasant Lake Paradise - Heaven w/private hot tub!
Apr 15 – 22
$355 per night
Superhost
Home in Beverly
Beverly Beach House- Upper Deck
Jul 31 – Aug 7
$400 per night
Guest favorite
Home in Marblehead
Modern 4 Bed 2 Bath home W/ Private outdoor space
Nov 6 – 13
$595 per night

Gloucester cottage rentals

Guest favorite
Cottage in Gloucester
Bright & Cheerful 3BR+den, Gloucester Cottage
Sep 23 – 30
$350 per night
Guest favorite
Cottage in Gloucester
SeaHaven Cottage at Stage Fort Park
Aug 30 – Sep 6
$332 per night
Guest favorite
Cottage in Rockport
Periwinkle Cottage #1 -walk to everything!
Apr 9 – 16
$201 per night
Guest favorite
Cottage in Kittery
Cozy Maine Cottage by the Sea
Jan 6 – 13
$147 per night
Guest favorite
Cottage in Newburyport
Plum Island’s TRUE NORTH COTTAGE
Jan 8 – 15
$625 per night
Guest favorite
Cottage in Rye
Seacoast Solo
Nov 10 – 17
$95 per night
Guest favorite
Cottage in Salem
Authentic 1739 Two Bdrm House in Salem
Mar 1 – 8
$208 per night
Guest favorite
Cottage in Newbury
Sunset Bliss a Plum Island Oasis- Beach 3 min walk
Jun 1 – 8
$462 per night
Guest favorite
Cottage in York
Adorable cottage by Shorts Sands Beach
Dec 19 – 26
$275 per night
Guest favorite
Cottage in Kittery
Charming Coastal Maine Cottage
May 22 – 29
$225 per night
Guest favorite
Cottage in Kittery
Badgers Island Cottage
Feb 13 – 20
$212 per night
Guest favorite
Cottage in York
Sweet cottage in quiet convenient coastal setting.
Sep 10 – 17
$296 per night

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.

  • 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 110 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 120 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.

  • 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 self check-in, over 10 homes with a gym, over 120 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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