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

Loft in Rockport

5.0 out of 5 average rating, 199 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

Mar 31 – Apr 7

G$32,478 GYD per night

Guest favorite

Apartment in Rockport

4.96 out of 5 average rating, 257 reviews

Harbor Retreat | Ocean View | Heart of Downtown

Discover Rockport's Harbor View Apartment! 🌊 This newly renovated 1-bedroom on the second level boasts stunning harbor views from a private deck. Steps from Bearskin Neck, enjoy proximity to unique shops 🛍️, fine dining 🍽️, and beaches 🏖️. Equipped with high-speed WiFi, a 55" Smart TV, and a Murphy couch. Perfect for experiencing Rockport's vibrant atmosphere. Note: Guests must climb stairs and the downtown location can be lively and noisy 🌆. Book your unforgettable seaside escape today! ⚓

Dec 9 – 16

G$29,437 GYD per night

Guest favorite

Guest suite in Gloucester

4.98 out of 5 average rating, 376 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!

Nov 29 – Dec 6

G$59,690 GYD 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

Dec 4 – 11

G$25,616 GYD per night

Guest favorite

Cottage in Gloucester

4.97 out of 5 average rating, 101 reviews

Sunny & private cottage in Lanesville Village

Sunny private 2 bedroom cottage with large garden, deck,and great Lanesville location near the ocean. In the off-season, a quiet escape -perfect for focused work, writing, painting or reading, Please contact host for discounts on longer stays (of a week or more) Living room with large flat screen smart TV with Roku, fast internet, and lounge with pull out couch and pocket door for privacy. Dogs under 55 lbs allowed (no more than 2 ) no cats. Yard is not fenced in.

Nov 7 – 14

G$35,840 GYD 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.

Oct 9 – 16

G$41,670 GYD per night

Guest favorite

Apartment in Beverly

4.97 out of 5 average rating, 182 reviews

Garden City of the Northshore

Our charming newly renovated second floor apartment in Beverly, on Boston's Northshore, is minutes from beautiful beaches, ocean parks, bike trails, commuter rail and restaurants. Convenient to Salem. This comfy apartment has beautiful light and sea breezes to greet you in the morning. Original pine floors, antique furnishings along with updated, full kitchen and new tiled bathroom. Queen size new mattress in the bedroom. 4k TV with free HBO, Showtime, Netflex .

Dec 27 – Jan 3

G$25,867 GYD 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.

Aug 8 – 15

G$41,880 GYD per night

Guest favorite

Guest suite in Rockport

4.99 out of 5 average rating, 611 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.

Feb 12 – 19

G$26,224 GYD 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.

Nov 16 – 23

G$24,813 GYD 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 4 – 11

G$33,477 GYD 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 29 – Apr 5

G$45,452 GYD 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 Beverly

4.92 out of 5 average rating, 448 reviews

Private apartment 10 min to Salem!

Sep 1 – 8

G$29,781 GYD per night

Guest favorite

Apartment in Gloucester

4.93 out of 5 average rating, 107 reviews

Open Concept Eclectic Mod 3 BR

May 2 – 9

G$38,071 GYD per night

Guest favorite

Condo in Rockport

4.99 out of 5 average rating, 144 reviews

Bearskin Neck Rockport ★ Amazing Views ★ Parking

Nov 20 – 27

G$62,991 GYD per night

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