Gloucester vacation rentals

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Top-rated vacation rentals in Gloucester

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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.

Aug 18 – 25

ﺩ.ﺇ1,935 per night

Guest favorite

Loft in Rockport

5.0 out of 5 average rating, 198 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

Feb 9 – 16

ﺩ.ﺇ556 per night

Superhost

Guest suite in Beverly

4.85 out of 5 average rating, 658 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.

Aug 31 – Sep 7

ﺩ.ﺇ450 per night

Guest favorite

Condo in Rockport

4.99 out of 5 average rating, 143 reviews

Bearskin Neck Rockport ★ Amazing Views ★ Parking

From the deck of this New England vacation retreat enjoy amazing views of Rockport Harbor and the iconic Motif #1. Steps from delightful shops, restaurants, and ice cream & coffee shops, this recently updated 1-bedroom, 1-bathroom condo with rare, on-site parking is located in the heart of Rockport right on Bearskin Neck. Enjoy beautiful ocean breezes sipping coffee or cocktails on the deck of this sweet beach retreat nestled on the Atlantic coast. Come fall in love with charming Rockport!

Aug 22 – 29

ﺩ.ﺇ1,254 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!

Dec 19 – 26

ﺩ.ﺇ1,051 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

Feb 12 – 19

ﺩ.ﺇ451 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 19 – 26

ﺩ.ﺇ733 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 8 – 15

ﺩ.ﺇ737 per night

Guest favorite

Guest suite in Rockport

4.99 out of 5 average rating, 609 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 16 – 23

ﺩ.ﺇ462 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 21 – 28

ﺩ.ﺇ540 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.

Oct 15 – 22

ﺩ.ﺇ437 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

ﺩ.ﺇ592 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

Beauport Hotel Gloucester35 locals recommend

Cape Ann Whale Watch41 locals recommend

7 Seas Whale Watch19 locals recommend

Stage Fort Park and Beach45 locals recommend

Causeway Restaurant41 locals recommend

Seaport Grill31 locals recommend

Other great vacation rentals in Gloucester

Guest favorite

Apartment in Gloucester

4.93 out of 5 average rating, 107 reviews

Open Concept Eclectic Mod 3 BR

Apr 22 – 29

ﺩ.ﺇ670 per night

Guest favorite

Apartment in Beverly

4.97 out of 5 average rating, 180 reviews

Garden City of the Northshore

Dec 31 – Jan 7

ﺩ.ﺇ442 per night

Superhost

Home in Gloucester

4.94 out of 5 average rating, 124 reviews

Wonderful Rocky Neck home on Gloucester harbor

Mar 27 – Apr 3

ﺩ.ﺇ1,426 per night

Guest favorite

Apartment in Beverly

4.92 out of 5 average rating, 448 reviews

Private apartment 10 min to Salem!

Aug 23 – 30

ﺩ.ﺇ521 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

Jun 19 – 26

ﺩ.ﺇ974 per night

Guest favorite

Home in Gloucester

4.82 out of 5 average rating, 161 reviews

Gloucester Private Contemporary 4 bedrooms

Sep 20 – 27

ﺩ.ﺇ1,418 per night

Guest favorite

Home in Rockport

4.97 out of 5 average rating, 281 reviews

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

Jan 26 – Feb 2

ﺩ.ﺇ865 per night

Guest favorite

Apartment in Beverly

4.94 out of 5 average rating, 617 reviews

Beverly Farms Apartment “Homeport”

Feb 24 – Mar 3

ﺩ.ﺇ616 per night

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Gloucester house rentals

Superhost

Home in Gloucester

4.9 out of 5 average rating, 105 reviews

Gloucester Beach House, near Good Harbor Beach!

Dec 3 – 10

ﺩ.ﺇ727 per night

Superhost

Home in Gloucester

4.8 out of 5 average rating, 137 reviews

Gloucester getaway ocean escape

Nov 12 – 19

ﺩ.ﺇ837 per night

Guest favorite

Home in Salisbury

4.86 out of 5 average rating, 159 reviews

Spacious 2 bedrooms waterfront free parking &Wi-fi

Mar 13 – 20

ﺩ.ﺇ541 per night

Guest favorite

Home in Marblehead

4.91 out of 5 average rating, 172 reviews

Bungalow in Downtown Marblehead

Apr 30 – May 7

ﺩ.ﺇ500 per night

Guest favorite

Home in Kittery

4.95 out of 5 average rating, 428 reviews

water view property "The Little House"

Jan 28 – Feb 4

ﺩ.ﺇ557 per night

Guest favorite

Home in Lynn

4.91 out of 5 average rating, 226 reviews

Clean, spacious In-Law Suite -Near Everything

Nov 14 – 21

ﺩ.ﺇ534 per night

Guest favorite

Home in Ipswich

4.98 out of 5 average rating, 170 reviews

Stagehill Beach House

Jan 2 – 9

ﺩ.ﺇ1,893 per night

Superhost

Home in Salisbury

4.91 out of 5 average rating, 114 reviews

NEW 3BR home, incredible views - Beach across St

Feb 6 – 13

ﺩ.ﺇ690 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

ﺩ.ﺇ905 per night

Guest favorite

Cottage in Gloucester

4.86 out of 5 average rating, 157 reviews

Bright & Cheerful 3BR+den, Gloucester Cottage

Oct 2 – 9

ﺩ.ﺇ1,351 per night

Guest favorite

Cottage in Rockport

4.98 out of 5 average rating, 100 reviews

Periwinkle Cottage #1 -walk to everything!

Sep 11 – 18

ﺩ.ﺇ960 per night

Guest favorite

Cottage in Gloucester

4.85 out of 5 average rating, 157 reviews

SeaHaven Cottage at Stage Fort Park

Apr 25 – May 2

ﺩ.ﺇ1,480 per night

Guest favorite

Cottage in Rye

4.91 out of 5 average rating, 120 reviews

Seacoast Solo

Nov 26 – Dec 3

ﺩ.ﺇ396 per night

Guest favorite

Cottage in Newburyport

5.0 out of 5 average rating, 144 reviews

Plum Island’s TRUE NORTH COTTAGE

Sep 21 – 28

ﺩ.ﺇ2,465 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 22 – 29

ﺩ.ﺇ1,945 per night

Superhost

Cottage in Hampton

4.78 out of 5 average rating, 184 reviews

Cozy Cottage steps from Hampton Strip With Parking

Oct 27 – Nov 3

ﺩ.ﺇ410 per night

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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

Other great vacation rentals in Gloucester

Apartment in Gloucester

Apartment in Beverly

Home in Gloucester

Apartment in Beverly

Apartment in Gloucester

Home in Gloucester

Home in Rockport

Apartment in Beverly

Gloucester house rentals

Home in Gloucester

Home in Gloucester

Home in Salisbury

Home in Marblehead

Home in Kittery

Home in Lynn

Home in Ipswich

Home in Salisbury

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 Hampton

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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