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.

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Guest favorite

Apartment in Beverly

4.92 out of 5 average rating, 448 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.

May 6 – 13

$119 per night

Guest favorite

Loft in Rockport

5.0 out of 5 average rating, 197 reviews

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

Dec 17 – 24

$155 per night

Superhost

Barn in Essex

4.9 out of 5 average rating, 133 reviews

The Loft/free river cruise/discounted beach passes

The Loft is a peaceful place to stay, yet in the middle of it all. With your booking comes 1 free ticket for the Essex River Cruise and discounted Crane Beach passes. It offers, personal concierge service before & during the stay, additional cleaning & laundry service, picnic baskets, beach chairs & blankets & pre-arrival shopping service, all for a reasonable fee. It comes with great Wi-Fi, parking, a firepit, hammock, BBQ, badminton, and a screened in breezeway with a table for 4 and a desk.

Feb 23 – Mar 2

$104 per night

Guest favorite

Guest suite in Gloucester

4.98 out of 5 average rating, 375 reviews

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!

Jan 14 – 21

$249 per night

Guest favorite

Loft in Gloucester

4.9 out of 5 average rating, 167 reviews

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2024! We look forward to you visiting RockyNeck in Gloucester. You will be sure to enjoy various special activities and events this summer and fall. We are located in the "quiet end", on a private residential dead end street in a historic artist colony . Nearby public transportation, Audubon sites, cultural events, the Gloucester Stage Co and beaches . Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV

Oct 21 – 28

$113 per night

Guest favorite

Apartment in Gloucester

4.94 out of 5 average rating, 109 reviews

Walk to Good Harbor Beach

Newly renovated ground floor efficiency apartment with sliders/walkout to fenced backyard. Wifi and Netflix included. Most dogs okay, some breed restrictions apply. If you want to bring your dog please contact us prior to booking. Three night minimum for all stays. Space includes 1 bedroom with Queen size bed and Living Area with pull out couch. 2 adults will be most comfortable. 5 minute walk to Good Harbor Beach or Bass Rocks. 15 minute walk to Rocky Neck.

Sep 4 – 11

$175 per night

Guest favorite

Cottage in Essex

4.97 out of 5 average rating, 212 reviews

French Flair "Pied a Terre" Cottage on the Marsh

Sunny cottage with marsh views, under 5 minute walk to town. Eat on the water in one of the many village restaurants, rent a kayak or paddle board. Go "down river" like a local! Shop the world renowned antique stores or enjoy the local beaches. There are many unique places to visit in Gloucester, Manchester, Rockport, Ipswich, Salem and of course Boston. There is a Visitor Manual for your convenience and we would be happy to answer questions that you might have.

May 17 – 24

$175 per night

Guest favorite

Guest suite in Rockport

4.99 out of 5 average rating, 608 reviews

Halibut Point State Park. Nature Lovers Retreat

"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.

Mar 19 – 26

$109 per night

Guest favorite

Apartment in Rockport

4.9 out of 5 average rating, 144 reviews

Sweet short term rental in Rockport

Lovely hilltop unit located on private wooded property, steps away from 2 beaches. Built on a massive granite boulder, the property is one of kind with stunning seasonal views of the Atlantic. Fully equipped kitchen, flat screen TV, WiFi, and everything to make your stay pleasant and comfortable. We're a 7 minute drive from downtown Rockport and Gloucester, a 7 minute walk to Cape Hedge and Long Beaches.

Apr 18 – 25

$132 per night

Guest favorite

Guest suite in Rockport

4.87 out of 5 average rating, 197 reviews

Charming Studio in the Pines

This is a first floor, above ground, garden apartment in a private home and is located in a quiet neighborhood with the backyard nestled in the woods, just out side your sliding door. Flower gardens and bird feeders adds ambiance for relaxing in a private setting. The studio offers a kitchenette, dining nook, a full bathroom, a queen bed, plus a sofa. Also available is CableTV, Netflix and Wi Fi.

May 6 – 13

$104 per night

Guest favorite

Guesthouse in Gloucester

4.94 out of 5 average rating, 143 reviews

Jestina's Cottage - Next to Rocky Neck

Jestina's Cottage is walking distance to the Rocky Neck Art Colony, Gloucester Stage, restaurants, Niles Beach and a short bike ride to Good Harbor Beach. You’ll love the cottage because of the ambience and the location; you feel like you are lost in the woods of Maine but you are close to everything. The cottage is great for couples, solo adventurers, business travelers, and pet-friendly.

Oct 5 – 12

$141 per night

Guest favorite

Apartment in Gloucester

4.97 out of 5 average rating, 102 reviews

The Gilbert: 1-Bed downtown suite, walk to beach.

Come stay in Gloucester’s historic downtown district, in St. Peter’s Square, just one block from Pavilion Beach, Stacey Boulevard and the historic West End of Main Street. The Gilbert sleeps two (up to 3 with an air mattress). A perfect getaway for those in love with history and seaside living. The unit has a private entrance, king sized bed, kitchenette and private bath.

Mar 19 – 26

$190 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Gloucester vacation rentals

Laptop-friendly workspace

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

4.99 out of 5 average rating, 143 reviews

Bearskin Neck Rockport ★ Amazing Views ★ Parking

Dec 12 – 19

$258 per night

Guest favorite

Home in Gloucester

4.99 out of 5 average rating, 153 reviews

Rocky Neck Retreat 4 Bedroom/2Bath/Kitchen/Laundry

Aug 24 – 31

$459 per night

Guest favorite

Apartment in Beverly

4.97 out of 5 average rating, 179 reviews

Garden City of the Northshore

Nov 16 – 23

$104 per night

Superhost

Home in Gloucester

4.94 out of 5 average rating, 124 reviews

Wonderful Rocky Neck home on Gloucester harbor

Mar 24 – 31

$338 per night

Guest favorite

Home in Gloucester

4.82 out of 5 average rating, 161 reviews

Gloucester Private Contemporary 4 bedrooms

Aug 20 – 27

$366 per night

Guest favorite

Apartment in Gloucester

4.93 out of 5 average rating, 107 reviews

Open Concept Eclectic Mod 3 BR

May 26 – Jun 2

$165 per night

Guest favorite

Apartment in Gloucester

4.85 out of 5 average rating, 105 reviews

Bright One Bedroom Apartment 5 Min Walk From Beach

Oct 28 – Nov 4

$293 per night

Guest favorite

Home in Gloucester

4.96 out of 5 average rating, 121 reviews

Booking spring/summer-Overlooking Lobster Cove

May 4 – 11

$265 per night

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Gloucester house rentals

Guest favorite

Home in Rockport

4.97 out of 5 average rating, 281 reviews

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

May 7 – 14

$247 per night

Superhost

Home in Gloucester

4.9 out of 5 average rating, 105 reviews

Gloucester Beach House, near Good Harbor Beach!

Dec 23 – 30

$169 per night

Superhost

Home in Gloucester

4.8 out of 5 average rating, 137 reviews

Gloucester getaway ocean escape

Sep 20 – 27

$237 per night

Guest favorite

Home in Marblehead

4.91 out of 5 average rating, 172 reviews

Bungalow in Downtown Marblehead

Feb 23 – Mar 2

$125 per night

Guest favorite

Home in Ipswich

4.98 out of 5 average rating, 170 reviews

Stagehill Beach House

Dec 30 – Jan 6

$450 per night

Guest favorite

Home in Lynn

4.91 out of 5 average rating, 225 reviews

Clean, spacious In-Law Suite -Near Everything

Aug 12 – 19

$127 per night

Guest favorite

Home in Kittery

4.95 out of 5 average rating, 428 reviews

water view property "The Little House"

Dec 17 – 24

$132 per night

Guest favorite

Home in Beverly

4.91 out of 5 average rating, 116 reviews

Historic New England Arts & Crafts home

May 26 – Jun 2

$359 per night

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Gloucester cottage rentals

Guest favorite

Cottage in Manchester-by-the-Sea

4.95 out of 5 average rating, 343 reviews

Singing Beach Cottage in Manchester by the Sea

Aug 24 – 31

$215 per night

Guest favorite

Cottage in Gloucester

4.86 out of 5 average rating, 157 reviews

Bright & Cheerful 3BR+den, Gloucester Cottage

Jun 2 – 9

$330 per night

Guest favorite

Cottage in Rockport

4.98 out of 5 average rating, 100 reviews

Periwinkle Cottage #1 -walk to everything!

Sep 30 – Oct 7

$191 per night

Guest favorite

Cottage in Gloucester

4.85 out of 5 average rating, 157 reviews

SeaHaven Cottage at Stage Fort Park

Apr 22 – 29

$350 per night

Guest favorite

Cottage in Rye

4.91 out of 5 average rating, 120 reviews

Seacoast Solo

Jul 12 – 19

$95 per night

Guest favorite

Cottage in Newburyport

5.0 out of 5 average rating, 144 reviews

Plum Island’s TRUE NORTH COTTAGE

Mar 29 – Apr 5

$625 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

May 9 – 16

$462 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

$147 per night

Show all

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

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 240 house rentals to over 40 cottage 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 230 vacation rentals in West Gloucester, and over 310 vacation rentals in Annisquam.
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 cottage rentals in Gloucester?
Experience the best of Gloucester with our cottage rentals, starting at about $100 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 210 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Gloucester vacation rentals

Top-rated vacation rentals in Gloucester

Vacation rentals for every style

Houses

Apartments

Cottages

Popular amenities for Gloucester vacation rentals

Stay near Gloucester's top sights

Gloucester beach vacation rentals

Condo in Rockport

Home in Gloucester

Apartment in Beverly

Home in Gloucester

Home in Gloucester

Apartment in Gloucester

Apartment in Gloucester

Home in Gloucester

Gloucester house rentals

Home in Rockport

Home in Gloucester

Home in Gloucester

Home in Marblehead

Home in Ipswich

Home in Lynn

Home in Kittery

Home in Beverly

Gloucester cottage rentals

Cottage in Manchester-by-the-Sea

Cottage in Gloucester

Cottage in Rockport

Cottage in Gloucester

Cottage in Rye

Cottage in Newburyport

Cottage in Newbury

Cottage in Kittery

Quick stats about vacation rentals in Gloucester

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

What types of vacation rentals are available in Gloucester?

Where should I stay in Gloucester?

Are there vacation rentals with a dedicated workspace in Gloucester?

Are there pet-friendly vacation rentals in Gloucester?

Are there Gloucester vacation rentals on Airbnb with pools?

How much does it cost to stay in cottage rentals in Gloucester?

Do house rentals in Gloucester have a gym?

Do house rentals in Gloucester have self check-in?

Do house rentals in Gloucester have a bbq area?

Are there family-friendly house rentals in Gloucester?

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