362+ Vacation Rentals & Holiday Homes in Gloucester |
  1. USA
  2. Massachusetts
  3. Gloucester

Gloucester Accommodations - Hotels & Rentals

About Gloucester Vacation Rentals

Discover More than 362 Incredible Getaway Rentals Available in Gloucester. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Gloucester.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Gloucester, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Gloucester. The Average Size of Places to Stay Near Gloucester is 988.18 ft², with Prices Averaging US $519 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Gloucester. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

Show more
Show less

Top Hotels & Vacation Rentals in Gloucester

Type Count
Vacation Homes 243
Holiday Apartments 69
Cottages 23
Villas 3

Use these Quick Filters to Find a Vacation Rental in Gloucester

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Gloucester with Online Reservations.

Weather in Gloucester, MA

View the weather forecast for Gloucester before booking your Gloucester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities GloucesterGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World GloucesterGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Good Harbor Beach
Wingaersheek Beach
Hammond Castle
Maritime Gloucester
Stage Fort Park
Lucky 7 Arcade
Eastern Point Lighthouse
Niles Beach
The Gorton Theatre
Half Moon Beach
Mount Ann Park
Dogtown
Cape Ann Museum
Plum Cove Beach
Ravenswood Park
Sargent House Museum
Capt Bill & Sons Whale Watch
Fishermen's Memorial Monument
Cape Ann Historical Museum
Gloucester Unitarian Universalist Church

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Dogtown 543 Properties
Good Harbor Beach 458 Properties
Plum Cove Beach 323 Properties
Northeast Hospital Corporation - Addison Gilbert Campus 316 Properties
Annisquam 310 Properties
Cape Ann Museum 286 Properties
Cape Ann Historical Museum 284 Properties
Sargent House Museum 283 Properties
Schooner Adventure 282 Properties
Gloucester Unitarian Universalist Church 280 Properties
Lucky 7 Arcade 279 Properties
Magnolia 85 Properties

Frequently Asked Questions About Gloucester?

What are the top hotels, lake houses & vacation rentals in Gloucester?

We provide an array of great vacation destinations in Gloucester. If you are looking to stay in or around the Gloucester area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Gloucester:

How many Hotels & Vacation Rentals have private pools in Gloucester?

We have 1 Hotels & Vacation Rentals featuring a private pool in and near Gloucester. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Gloucester is best for families?

Searching for a family-friendly getaway in Gloucester? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Gloucester?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2026 is over 362 in the Gloucester area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Gloucester.

Nearby Neighborhood (1) 
Neighborhood Property Count
Annisquam Vacation Rentals in Gloucester, Massachusetts 310

People Also Ask

Online Reservation in Gloucester

Recently Booked Hotels, Resorts, or Rentals in Gloucester