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.
Sep 15 – 22
$469 per night
4.99 out of 5 average rating, 153 reviews
Guest favorite
Condo in Rockport
6 Tuna Wharf - Harbor right outside kitchen door!
Dreaming of summer vacation in Rockport? This condo is in the middle of the action and excitement of Bearskin Neck yet private & directly on the wharf. Classy beachy condo overlooking Rockport Harbor & Motif 1. Steps from shops, beaches, restaurants, art galleries & beaches. Outside the kitchenette, a private patio on the wharf for morning coffee, grilling or evening happy hour. Relax and watch the boats go by year round! A fun getaway even in the off season. Book early to secure your trip!
Feb 17 – 24
$299 per night
4.99 out of 5 average rating, 184 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.
Oct 31 – Nov 7
$265 per night
4.96 out of 5 average rating, 121 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
Guesthouse in Rockport
Sea Mist Cottage Rockport, MA
Dec 11 – 18
$176 per night
5.0 out of 5 average rating, 214 reviews
Guest favorite
Guest suite in Gloucester
The Carriage House near Plum Cove Beach
Dec 30 – Jan 6
$225 per night
4.98 out of 5 average rating, 128 reviews
Guest favorite
Apartment in Beverly
Garden City of the Northshore
May 2 – 9
$110 per night
4.97 out of 5 average rating, 176 reviews
Guest favorite
Apartment in Rockport
Mary's By The Sea
Feb 16 – 23
$167 per night
4.94 out of 5 average rating, 148 reviews
Guest favorite
Apartment in Beverly
Private apartment 10 min to Salem!
Apr 13 – 20
$119 per night
4.92 out of 5 average rating, 445 reviews
Guest favorite
Guest suite in Beverly
The Garden Bed
May 1 – 8
$121 per night
4.99 out of 5 average rating, 147 reviews
Guest favorite
Apartment in Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
Oct 10 – 17
$352 per night
4.78 out of 5 average rating, 200 reviews
Guest favorite
Tiny home in Rockport
Little Red House on Bearskin Neck!
Nov 22 – 29
$180 per night
4.94 out of 5 average rating, 128 reviews
Superhost
Home in Gloucester
Gloucester getaway ocean escape
Jun 26 – Jul 3
$183 per night
4.8 out of 5 average rating, 137 reviews
Guest favorite
Loft in Rockport
Chic Downtown Loft ☆ Private Parking ☆ Ocean View
Oct 25 – Nov 1
$221 per night
5.0 out of 5 average rating, 192 reviews
Guest favorite
Townhouse in Gloucester
Between 2 Beaches
Jan 14 – 21
$488 per night
5.0 out of 5 average rating, 150 reviews
Superhost
Home in Gloucester
Gloucester Beach House, near Good Harbor Beach!
Apr 3 – 10
$169 per night
4.9 out of 5 average rating, 104 reviews

Gloucester house rentals

Guest favorite
Home in Rockport
Charming Toe-Hold, A Short Walk to Town and Beach
Feb 27 – Mar 6
$204 per night
4.97 out of 5 average rating, 279 reviews
Guest favorite
Home in Ipswich
Stagehill Beach House
Nov 16 – 23
$450 per night
4.98 out of 5 average rating, 170 reviews
Guest favorite
Home in Marblehead
Bungalow in Downtown Marblehead
Jan 5 – 12
$125 per night
4.91 out of 5 average rating, 169 reviews
Guest favorite
Home in Lynn
Clean, spacious In-Law Suite -Near Everything
Jan 10 – 17
$127 per night
4.91 out of 5 average rating, 225 reviews
Guest favorite
Home in Beverly
Historic New England Arts & Crafts home
Nov 19 – 26
$359 per night
4.91 out of 5 average rating, 116 reviews
Guest favorite
Home in Windham
One Level 2 bedroom suite on private cul-de-sac
May 11 – 18
$123 per night
4.93 out of 5 average rating, 256 reviews
Guest favorite
Home in Salisbury
NEW 3BR home, incredible views - Beach across St
Oct 17 – 24
$214 per night
4.91 out of 5 average rating, 113 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 Rye
*Beachfront* Vintage Coastal Cottage - Relaxation
Nov 22 – 29
$198 per night
4.99 out of 5 average rating, 215 reviews
Guest favorite
Home in Billerica
Residential home ▪ Billerica ▪ quiet, clean & cozy
Dec 22 – 29
$133 per night
4.97 out of 5 average rating, 148 reviews
Guest favorite
Home in Marblehead
Modern 4 Bed 2 Bath home W/ Private outdoor space
Dec 18 – 25
$291 per night
4.88 out of 5 average rating, 128 reviews
Guest favorite
Home in Kittery
water view property "The Little House"
Dec 17 – 24
$132 per night
4.95 out of 5 average rating, 421 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 Gloucester
Bright & Cheerful 3BR+den, Gloucester Cottage
Apr 20 – 27
$329 per night
4.86 out of 5 average rating, 157 reviews
Guest favorite
Cottage in Rockport
Periwinkle Cottage #1 -walk to everything!
Apr 5 – 12
$186 per night
4.98 out of 5 average rating, 100 reviews
Guest favorite
Cottage in Rye
Seacoast Solo
Jul 17 – 24
$95 per night
4.91 out of 5 average rating, 120 reviews
Guest favorite
Cottage in Newburyport
Plum Island’s TRUE NORTH COTTAGE
Jan 6 – 13
$625 per night
5.0 out of 5 average rating, 144 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 Newbury
Sunset Bliss a Plum Island Oasis- Beach 3 min walk
Jun 19 – 26
$462 per night
4.82 out of 5 average rating, 101 reviews
Superhost
Cottage in Hampton
Cozy Cottage steps from Hampton Strip With Parking
Dec 13 – 20
$84 per night
4.78 out of 5 average rating, 183 reviews
Guest favorite
Cottage in Kittery
Badgers Island Cottage
Jan 6 – 13
$212 per night
4.94 out of 5 average rating, 124 reviews
Guest favorite
Cottage in Kittery
Charming Coastal Maine Cottage
Dec 12 – 19
$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 20 – 27
$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!
Sep 17 – 24
$289 per night
4.95 out of 5 average rating, 216 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

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