Compare Gloucester Vacation Rentals

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Gloucester Rentals

Long Beach Suites

Long Beach Suites

2 out of 5
28 Rockport Rd, Gloucester, MA
2.32 mi from city center
$322 nightly
The price is $360 total per night
$360 total
Oct 13 - Oct 14
Total with taxes and fees
At this aparthotel, guests have access to features like express check-out. If you drive, put free parking to good use.
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

3.55 mi from city center
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

3.08 mi from city center
$1,367 nightly
The price is $1,526 total per night
$1,526 total
Oct 5 - Oct 6
Total with taxes and fees
At this vacation home, guests have access to a hot tub, an arcade/game room, and laundry facilities. Other amenities at this beach vacation home include a garden and barbecue grills.
Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

1.2 mi from city center
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

12.92 mi from city center
$879 nightly
The price is $1,005 total per night
$1,005 total
Nov 4 - Nov 5
Total with taxes and fees
At this condo, guests have access to features like laundry facilities.
Apartments in Salem

Apartments in Salem

3 out of 5
40-42 Dow Street, Salem, MA
13.3 mi from city center
$440 nightly
The price is $484 total per night
$484 total
Nov 3 - Nov 4
Total with taxes and fees
A local mainstay since 1915, Apartments in Salem offers free WiFi in public areas, express check-in, and express check-out. You'll find limited parking. Staff members can help with accommodation requests, and provide luggage storage.
Leslie's Retreat: Spacious home ideally located to everything

Leslie's Retreat: Spacious home ideally located to everything

13.32 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden. Friendly staff can provide concierge services, and also offer advice about sightseeing.
House near down town Salem

House near down town Salem

13.34 mi from city center
$623 nightly
The price is $695 total per night
$695 total
Oct 12 - Oct 13
Total with taxes and fees
At this vacation home, guests have access to barbecue grills.
7 Beachside Inn

7 Beachside Inn

3 out of 5
7 H st, Hampton, NH
21.76 mi from city center
$375 nightly
The price is $403 total per night
$403 total
Oct 9 - Oct 10
Total with taxes and fees
At 7 Beachside Inn, guests have access to features like a seasonal outdoor pool. You can take advantage of free parking if you drive. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area.
Ocean Breeze -Dog Friendly Cottage Steps 2 Beach Sleeps 6 - 100 yards to Beach!

Ocean Breeze -Dog Friendly Cottage Steps 2 Beach Sleeps 6 - 100 yards to Beach!

22.17 mi from city center
$306 nightly
The price is $332 total per night
$332 total
Oct 13 - Oct 14
Total with taxes and fees
Guests of this cottage enjoy access to a water park, laundry facilities, and barbecue grills.
Ocean views from every window. 5min walk to the quiet end of the beach!

Ocean views from every window. 5min walk to the quiet end of the beach!

22.31 mi from city center
This condo is a smoke-free condo building.
RV Camper - Few Min to the Beach -Boston Downtown and Logan Airport With parking

RV Camper - Few Min to the Beach -Boston Downtown and Logan Airport With parking

2 out of 5
22.42 mi from city center
Guests staying at RV Camper - Few Min to the Beach -Boston Downtown and Logan Airport With parking enjoy a water park, a garden, and a living plant wall.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Gloucester Large Group Rentals

How to Book Vacation Rentals in Gloucester



🏠 What is the best price for Gloucester vacation rentals?

Gloucester vacation rentals range in price, starting at $332 per night.


🏠 What types of vacation rentals in Gloucester can I rent?

Orbitz offers a wide range of Gloucester rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Gloucester condo rentals.


🏠 Is it free to cancel my Gloucester vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Gloucester vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Gloucester. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Gloucester?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Gloucester apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Gloucester?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Gloucester package deals will get you even more savings.

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More to Explore