Search
Best rentals
Tips
FAQs
Map

Gloucester vacation rentals

Search hundreds of travel sites at once for car rental deals in Gloucester

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Best Gloucester vacation rentals

Most recommended vacation rentals in Gloucester

Show all
Calder 2 - Gloucester - Living room
Calder 2
9.4 Wonderful
C$ 406+
C$ 406+
Parking
Free Wi-Fi
Ocean Breeze-8min Walk to Beach - Gloucester - Living room
Ocean Breeze-8min Walk to Beach
9.5 Wonderful
C$ 381+
C$ 381+
Parking
Free Wi-Fi
Bianca's House
4.4 Mediocre
C$ 374+
C$ 374+
Free Wi-Fi

When to book a vacation rental in Gloucester

Price per night / rental. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for finding Gloucester vacation rental deals

  • Gloucester, MA is considered the birthplace of the entire U.S. fishing industry, so if you love to fish, searching for one of the Gloucester vacation rentals that will let you get a line in the water should be a top priority. An option like Ocean Breeze will put you within 10 minutes of Good Harbor Beach and within 15 minutes of Long Beach.
  • When you walk into The Duval House in Gloucester, it isn’t going to feel like Gloucester much at all. It’s been decorated with a Key West theme on the interior to make it feel like you’re on vacation from the second you step inside. But you’ll also be situated in a place that’ll make it easy to explore everything Gloucester has to offer since it’s within walking distance of many restaurants, shops, and more.
  • Another one of the vacation rentals that will put you close to downtown Gloucester is this rental that is Steps to Downtown Gloucester. You can get to a variety of local establishments by walking to places like the Cape Ann Museum and Sargent House Museum. It’s also just a few blocks away from the beach.
  • Gloucester is a city that has been around for almost 400 years, so it’s filled with all kinds of history that you might want to explore. An easy way to do it is by staying in one of the Gloucester vacation rentals that’s on the older side, such as this Apartment in a historic home across from Cripple Cove Harbour.
  • If you’re in search of Gloucester house rentals steeped in New England charm, Drift Accommodations has it. It also features contemporary decor thrown into the mix along with a wide range of little luxuries like a fully stocked kitchen, large glass sliding doors, memory foam mattresses, and more. It offers a private balcony as well that provides great views of the sunrises and sunsets.
  • Pool is the most popular vacation rental property amenity in Gloucester
  • Vacation rentals in Gloucester are around 36% more expensive than hotels on average. Search here to compare prices for all accommodation types in Gloucester.
  • The best vacation rental properties in Gloucester are Hidden Gem - 3 Minute Walk to Beach (10.0, 30 reviews), Luxury Accommodations in Quiet Seaside Village (10.0, 32), and Romantic Summerwind Cottage, Scenic Harbor View w/Spacious Deck! (10.0, 31), based on ratings and reviews from real travelers.
  • Book your Gloucester vacation rental at least 33 days before your stay begins to get the best price.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Gloucester for 6 days.

FAQs when booking a vacation home in Gloucester

  • How much is a vacation rental for a week in Gloucester?

    The average price for a weekly Gloucester vacation rental found by KAYAK users in the last 2 weeks is C$ 3,523.

  • How much is a vacation rental for a month in Gloucester?

    The average price for a monthly Gloucester vacation rental found by KAYAK users in the last 2 weeks is C$ 15,099.

  • What types of vacation rentals are available in Gloucester?

    in Gloucester you’ll find that most vacation rentals are houses.

  • Are there any pet-friendly vacation rentals in Gloucester?

    There are a number of dog and pet-friendly Gloucester vacation rentals, with around 10% allowing you to bring your pet along with you.

  • How much is a vacation rental in Gloucester?

    KAYAK users have found vacation rentals in Gloucester for as cheap as C$ 207 in the last 3 days. The average price is C$ 503.

  • How much is a vacation rental in Gloucester for tonight?

    In the last 72 hours, users have found Gloucester vacation rentals for tonight for as low as C$ 649. Search here for similar prices

  • How much is a vacation rental in Gloucester for this weekend?

    In the last 72 hours, users have found Gloucester vacation rentals for this weekend for as low as C$ 471 per night. Search here for similar prices

  • How can I find vacation rentals near me in Gloucester?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

  • Which vacation rentals in Gloucester work best for quick getaways?

    Many of the Gloucester vacation rentals that are available would be good options for those trying to take a quick getaway. But there is a Charming Studio that would be ideal for couples looking to get away for a day or two, writers looking for a quiet place to work, or anyone else who just needs a little peace and quiet.

  • What is the trendiest vacation rental in Gloucester?

    A lot of the vacation rentals that are scattered throughout Gloucester have some history to them. There are, however, some like Loft On Main that are starting to take on a trendier look and feel. This centrally located house rental is just steps from the downtown area, and it features a very modern design on the interior.

  • Are there any Gloucester home rentals that will provide a unique experience?

    The Calder 2 is a special vacation rental in that many of the rooms in it are covered with wood from top to bottom in an aesthetically pleasing way. It also has a very private master bedroom stashed in the attic where you won’t have to worry about being disturbed.

  • Where should I stay in Gloucester if I want to unplug and unwind?

    Almost all the different vacation rentals in Gloucester will set you up with free Wi-Fi when you’re staying in them. If you’d prefer not to have Wi-Fi or even a TV for that matter, the La Bohème Retreat is the place to unplug from the rest of the world and unwind. It creates the right setting for those who need to recharge.

Where to stay in Gloucester?

Our map will help you find the perfect place to stay in Gloucester by showing you the exact location of each vacation rental.