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

4.99 out of 5 average rating, 153 reviews

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 20 – 27

R10,559 ZAR per night
Guest favorite

Apartment in Beverly

4.92 out of 5 average rating, 446 reviews

Private apartment 10 min to Salem!

This private entrance basement apartment is within a 1/2 mile to several beautiful Beverly beaches. Downtown Beverly is about a 10 to 15 minute pleasant walk. It offers great restaurants and cafes. Live entertainment is happening almost nightly at the Larcom and Cabot theaters. Endicott College is 1 mile away. Downtown Salem is about a ten minute drive from here. The train to Boston, Salem, or Rockport is about a mile away. Plenty of safe street parking is available in front of my house.

Apr 7 – 14

R2,288 ZAR per night
Superhost

Guest suite in Beverly

4.85 out of 5 average rating, 656 reviews

Historic North Shore, private suite & bathroom

Minutes from Salem! Relax in historic Beverly (walk to Beverly shops) in your private suite; bedroom, living room, and small bathroom, connected to our home, but private entrance. Just minutes from Salem. Commuter line to Boston and close to beautiful North Shore beaches and historic sites. Beaches within biking and driving distances, downtown, parks, hiking. Comfy, soft king bed, queen pull out couch, and plenty of linens. Great for couples, solo adventurers, business travelers, and families.

Sep 11 – 18

R2,301 ZAR 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

Apartment in Beverly

4.97 out of 5 average rating, 176 reviews

Garden City of the Northshore

Nov 13 – 20

R2,270 ZAR per night
Guest favorite

Apartment in Gloucester

4.86 out of 5 average rating, 104 reviews

Bright One Bedroom Apartment 5 Min Walk From Beach

Nov 12 – 19

R5,599 ZAR per night
Guest favorite

Home in Gloucester

4.82 out of 5 average rating, 161 reviews

Gloucester Private Contemporary 4 bedrooms

Aug 4 – 11

R7,958 ZAR per night
Guest favorite

Condo in Rockport

4.99 out of 5 average rating, 184 reviews

6 Tuna Wharf - Harbor right outside kitchen door!

Feb 23 – Mar 2

R6,515 ZAR per night
Guest favorite

Home in Gloucester

4.96 out of 5 average rating, 121 reviews

Booking spring/summer-Overlooking Lobster Cove

Oct 24 – 31

R5,774 ZAR per night
Guest favorite

Apartment in Gloucester

4.94 out of 5 average rating, 105 reviews

Open Concept Eclectic Mod 3 BR

Apr 22 – 29

R3,455 ZAR per night
Guest favorite

Apartment in Rockport

4.94 out of 5 average rating, 148 reviews

Mary's By The Sea

Mar 17 – 24

R3,630 ZAR per night
Guest favorite

Loft in Rockport

5.0 out of 5 average rating, 194 reviews

Chic Downtown Loft ☆ Private Parking ☆ Ocean View

Oct 28 – Nov 4

R4,966 ZAR per night
Guest favorite

Townhouse in Gloucester

5.0 out of 5 average rating, 152 reviews

Between 2 Beaches

Jan 7 – 14

R10,417 ZAR per night
Guest favorite

Guesthouse in Rockport

5.0 out of 5 average rating, 214 reviews

Sea Mist Cottage Rockport, MA

Oct 24 – 31

R4,204 ZAR per night
Guest favorite

Tiny home in Rockport

4.94 out of 5 average rating, 128 reviews

Little Red House on Bearskin Neck!

Jul 4 – 11

R4,272 ZAR per night
Superhost

Home in Gloucester

4.9 out of 5 average rating, 105 reviews

Gloucester Beach House, near Good Harbor Beach!

Oct 14 – 21

R5,850 ZAR per night

Gloucester house rentals

Guest favorite

Home in Rockport

4.97 out of 5 average rating, 279 reviews

Charming Toe-Hold, A Short Walk to Town and Beach

May 10 – 17

R5,376 ZAR per night
Guest favorite

Home in Marblehead

4.91 out of 5 average rating, 169 reviews

Bungalow in Downtown Marblehead

Nov 11 – 18

R2,723 ZAR per night
Guest favorite

Home in Ipswich

4.98 out of 5 average rating, 170 reviews

Stagehill Beach House

Apr 21 – 28

R9,450 ZAR per night
Guest favorite

Home in Lynn

4.91 out of 5 average rating, 225 reviews

Clean, spacious In-Law Suite -Near Everything

Feb 25 – Mar 4

R2,754 ZAR per night
Guest favorite

Home in Rye

4.99 out of 5 average rating, 218 reviews

*Beachfront* Vintage Coastal Cottage - Relaxation

Oct 30 – Nov 6

R4,716 ZAR per night
Guest favorite

Home in Kittery

4.95 out of 5 average rating, 424 reviews

water view property "The Little House"

Oct 13 – 20

R2,870 ZAR per night
Guest favorite

Home in Marblehead

4.98 out of 5 average rating, 185 reviews

Authentic Rustic Single Family Home in Old Town

Jan 12 – 19

R5,465 ZAR per night
Superhost

Home in Salisbury

4.91 out of 5 average rating, 113 reviews

NEW 3BR home, incredible views - Beach across St

Apr 25 – May 2

R4,780 ZAR per night
Guest favorite

Home in Billerica

4.97 out of 5 average rating, 149 reviews

Residential home ▪ Billerica ▪ quiet, clean & cozy

Mar 18 – 25

R2,912 ZAR per night
Guest favorite

Home in North Andover

4.94 out of 5 average rating, 127 reviews

Nana-tucket Inn

Oct 17 – 24

R16,302 ZAR per night
Guest favorite

Home in Marblehead

4.88 out of 5 average rating, 131 reviews

Modern 4 Bed 2 Bath home W/ Private outdoor space

Jan 9 – 16

R6,515 ZAR per night
Guest favorite

Home in Beverly

4.91 out of 5 average rating, 116 reviews

Historic New England Arts & Crafts home

Dec 11 – 18

R7,827 ZAR per night

Gloucester cottage rentals

Guest favorite

Cottage in Essex

4.97 out of 5 average rating, 212 reviews

French Flair "Pied a Terre" Cottage on the Marsh

Aug 23 – 30

R3,801 ZAR per night
Guest favorite

Cottage in Gloucester

4.86 out of 5 average rating, 157 reviews

Bright & Cheerful 3BR+den, Gloucester Cottage

May 8 – 15

R7,169 ZAR per night
Guest favorite

Cottage in Gloucester

4.85 out of 5 average rating, 157 reviews

SeaHaven Cottage at Stage Fort Park

Jul 30 – Aug 6

R7,244 ZAR per night
Guest favorite

Cottage in Rockport

4.98 out of 5 average rating, 100 reviews

Periwinkle Cottage #1 -walk to everything!

May 4 – 11

R4,951 ZAR per night
Guest favorite

Cottage in Rye

4.91 out of 5 average rating, 120 reviews

Seacoast Solo

Jan 30 – Feb 6

R1,966 ZAR per night
Superhost

Cottage in Hampton

4.78 out of 5 average rating, 183 reviews

Cozy Cottage steps from Hampton Strip With Parking

Jan 6 – 13

R1,837 ZAR per night
Guest favorite

Cottage in Newburyport

5.0 out of 5 average rating, 144 reviews

Plum Island’s TRUE NORTH COTTAGE

Jan 2 – 9

R13,576 ZAR per night
Guest favorite

Cottage in Kittery

4.95 out of 5 average rating, 139 reviews

Cozy Maine Cottage by the Sea

Oct 27 – Nov 3

R3,201 ZAR per night
Guest favorite

Cottage in Newbury

4.82 out of 5 average rating, 101 reviews

Sunset Bliss a Plum Island Oasis- Beach 3 min walk

Aug 27 – Sep 3

R10,029 ZAR per night
Guest favorite

Cottage in Kittery

4.96 out of 5 average rating, 272 reviews

Charming Coastal Maine Cottage

Oct 17 – 24

R4,900 ZAR per night
Guest favorite

Cottage in Kittery

4.94 out of 5 average rating, 124 reviews

Badgers Island Cottage

Jan 12 – 19

R4,626 ZAR per night
Guest favorite

Cottage in Salem

4.97 out of 5 average rating, 137 reviews

Authentic 1739 Two Bdrm House in Salem

Aug 23 – 30

R5,952 ZAR 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.

  • 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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  4. Essex County
  5. Gloucester