Gloucester vacation rentals

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Best Gloucester vacation rentals

Most recommended vacation rentals in Gloucester

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Radiant Gloucester House with Private Porch! - Gloucester - Living room
Radiant Gloucester House with Private Porch!
Gloucester, VA
9.6Wonderful(13)
Free Wi-Fi
Pet friendly
$314+
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Relaxing Riverfront Cottage with Boat Dock! - Gloucester - Living room
Relaxing Riverfront Cottage with Boat Dock!
Gloucester, VA
Free Wi-Fi
$264+
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\'Bee Haven\' Cottage Retreat Near Colonial Williamsburg - Gloucester - Living room
\'Bee Haven\' Cottage Retreat Near Colonial Williamsburg
Gloucester, VA
Pet friendly
$173+
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Eclectic Apartment- 2-4 friends- Family centered. Safe Neighborhood - Gloucester - Bedroom
Eclectic Apartment- 2-4 friends- Family centered. Safe Neighborhood
Gloucester, VA
$132+
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Cozy Country setting with comforts of home - Gloucester - Dining room
Cozy Country setting with comforts of home
Gloucester, VA
$254+
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Welcome to this Waterfront Home with Amazing Views\n - Gloucester - Kitchen
Welcome to this Waterfront Home with Amazing Views\n
Gloucester, VA
$285+
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Gloucester Retreat with Backyard Oasis and Pier! - Gloucester - Patio
Gloucester Retreat with Backyard Oasis and Pier!
Gloucester, VA
9.3Wonderful(26)
Free Wi-Fi
$653+
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Right On Main St! Shops, Arts, Dining And More! - Gloucester - Living room
Right On Main St! Shops, Arts, Dining And More!
Gloucester, VA
Free Wi-Fi
Pet friendly
$186+
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L'Hermione - Gloucester - Balcony
L'Hermione
Gloucester, VA
8.0Very good(4)
$713+
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Waterfront Gloucester Cottage with Private Boat Dock - Gloucester - Patio
Waterfront Gloucester Cottage with Private Boat Dock
Gloucester, VA
9.2Wonderful(4)
Free Wi-Fi
$461+
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Relax, Recharge And EnjoyNear Williamsburg Walk To Restaurants and Shops - Gloucester - Building
Relax, Recharge And EnjoyNear Williamsburg Walk To Restaurants and Shops
Gloucester, VA
$337+
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Riverside farm cottage with pool - Gloucester
Riverside farm cottage with pool
Gloucester, VA
Pool
$271+
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Cozy Gloucester Getaway w/ Porch & Sunroom! - Gloucester
Cozy Gloucester Getaway w/ Porch & Sunroom!
Gloucester, VA
9.7Wonderful(24)
$237+
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Amazing Waterfront Getawaylong Term Renters Are Welcome! - Gloucester
Amazing Waterfront Getawaylong Term Renters Are Welcome!
Gloucester, VA
$509+
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Private Retreat - Wareloch a Waterfront Estate in Tidewater - Gloucester
Private Retreat - Wareloch a Waterfront Estate in Tidewater
Gloucester, VA
$769+
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Enjoy The Simple Life In This Luxury Farmhouse Near Williamsburg - Gloucester
Enjoy The Simple Life In This Luxury Farmhouse Near Williamsburg
Gloucester, VA
9.6Wonderful(15)
$295+
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Good to know

Low season

November

High season

January

Average price (weeknight)

$227

Average price (weekend night)

$228
Cheapest month to stay with an average 24% drop in price.
Most expensive month to stay with an average 24% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Gloucester vacation rental deals

  • The best vacation rental properties in Gloucester are Riverside farm cottage with pool (10.0, 20 reviews), Welcome to \'The Happy Soul\' (10.0, 47), and The River House Getaway! Come Relax and Enjoy! (10.0, 34), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Gloucester, you should consider visiting during the low season. The cheapest vacation homes in Gloucester can be found in November and April.
  • The cheapest night for renting a vacation home in Gloucester is Tuesday. In contrast, the most expensive is Wednesday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Gloucester for 3 days.

FAQs when booking a vacation home in Gloucester

  • What types of vacation rentals are available in Gloucester?

    There are loads of different property types that you can make your vacation home in Gloucester. You’ll find campgrounds, condos, cottages and houses.

  • What are some of the most-loved vacation rentals available in Gloucester?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Chesapeake Bay Rv Resort.

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

    There are a number of dog and pet-friendly Gloucester vacation rentals, with around 14% allowing you to bring your pet along with you.

  • 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.

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.

Everything you need to know for your stay in Gloucester

Gloucester vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Gloucester. Find cheap vacation homes to rent in Gloucester. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Gloucester that suits you best.

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