Holiday rentals in Gloucester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Gloucester

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

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.

4–11 Sep

$754 SGD per night

Guest favourite

Flat 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! ⚓

29 Oct – 5 Nov

$236 SGD per night

Superhost

Barn in Essex

4.9 out of 5 average rating, 133 reviews

The Loft/ Salt Marsh Views/Downtown Location

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.

13–20 Nov

$164 SGD per night

Guest favourite

Apartment 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!

6–13 Nov

$403 SGD per night

Superhost

Home in Gloucester

4.94 out of 5 average rating, 124 reviews

Wonderful Rocky Neck home on Gloucester harbor

2 Bedroom with Loft, 1 Bathroom fully furnished Home on Gloucester harbor. Dead end street with 3 off street parking spots. Restaurants, local art gallery's, the beach all just a short walk away. Wake up with the sweet smell of ocean air and the sound of seagulls calling. Enjoy your breakfast with a million dollar view on the 4 season porch with 8 sliding windows overlooking the harbor. You could spend hours watching the boats go by as you read a good book with your fur baby on your lap.

28 Mar – 4 Apr

$529 SGD per night

Guest favourite

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!

8–15 Feb

$390 SGD per night

Guest favourite

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

27 Dec – 3 Jan

$167 SGD per night

Guest favourite

Flat 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.

18–25 Sep

$272 SGD per night

Guest favourite

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.

14–21 Jan

$171 SGD per night

Guest favourite

Flat 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.

22–29 Apr

$198 SGD per night

Guest favourite

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.

24–31 Dec

$162 SGD per night

Guest favourite

Guest house 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.

2–9 Oct

$220 SGD per night