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Gloucester, Massachusetts Vacation Rentals

59 listings found
About Gloucester, Massachusetts

A charming town on Cape Ann in Massachusetts, Gloucester resort community, is the perfect destination for a wonderful New England vacation. Natural beauty abounds outside your vacation house in Gloucester, Massachusetts. There is a plethora of natural beauty in the area, providing a very serene environment surrounding your Gloucester condominium. If you and your family seek a destination full of natural beauty, countless activities to fill your days and the opportunity to find a rare moment of peaceful solitude that is so often sought in this all too often chaotic world your wonderful Gloucester vacation will deliver you just that.

Gloucester Activities

You will discover ample opportunities to fill your days with a variety of activities and something can be found that will amuse each member of the family, when they are not relaxing in your luxury vacation house in Gloucester, Massachusetts. Your Gloucester rental will bring you to a town full of charm and warmth. After waking in your luxurious condominium in Gloucester you will not find yourself at a loss for amusement. Leave your Gloucester condo rental in the morning and head to Hammond Castle or Beauport Mansion for some amazing tours. Spend some time shopping in the quaint shops before returning for an evening of family bonding in your Gloucester vacation rental. Make a day of it by taking the family out for a day of whale watching or on a deep-sea fishing charter. Plan a day exploring historic Boston, walk along The Freedom Trail and then get a delicious dinner of fresh seafood at a five star restaurant before returning to your condominium in Gloucester for an amazing nights rest. Leave your Gloucester condo behind and venture out for a day on the beautiful shores of the Atlantic Ocean. If you love art you must visit the Rocky Neck artists’ colony. A stay in a Gloucester condo rental wouldn’t be complete without a trip to The Cape Ann Museum, a great activity for a rainy day that the kids will love.  Your Gloucester rental gives you a great destination in a beautiful town with a friendly welcoming atmosphere and the convenience of being within a short drive to all the excitement of Boston. Gloucester resort community will truly provide you with activities to satisfy your every desire.

Gloucester Vacation Rentals

A Gloucester house rental can provide you and your family with everything you need to make your Gloucester vacation memorable. Whatever you seek in your Gloucester vacation rental, it can be easily found. If you seek a luxury Gloucester house rental large enough for the entire family or an intimate condominium in Gloucester for two for a romantic getaway weekend, Gloucester resort community will be able to deliver. A Gloucester condo rental will provide you with a peaceful environment in which to enjoy your Massachusetts vacation. You will find a myriad of different choices for a Gloucester rental. No matter which you desire, a beautiful luxury Gloucester condominium or a Gloucester house rental with every creature comfort of home, your vacation house in Gloucester will be all that you and your family dream of for a Massachusetts vacation to remember.

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Rate & Availability Disclaimer
Base rates (EXCLUDING any applicable taxes, fees, and promotions) are displayed as provided by rental managers and are not guaranteed. Rates are based on the start date or arrival date selected in the search and may vary on subsequent days. Properties marked ‘Available’ or ‘Booked’ are done so based on information provided by the rental manager and are not guaranteed. For completed details (including minimum stay length, full availability information, approved arrival days and other booking rules for the property) select ‘Book Now” (on available properties) or ‘Check Availability’ (booked properties) to be directed to the rental manager’s website or click “Contact” to send them a specific request.

Heart of Back Bay! Close to Prudential Center and The T!

Outstanding 2 Bed Apt in Heart of Back Bay!

Stylish Flex-cation Space in Back Bay!

Boston Back Bay Apt with fast wifi & great extras!

Heart of Back Bay! Close to Prudential Center and The T!

Bright Condo, Plenty of Room, Sleeps Upto 8

2 Bed with Work From Anywhere Office & Fast Wifi!

Perfect Location! Great Amenities Included!

Outstanding Upgraded Luxury Apt!

Outstanding Upgraded Luxury Apt!

Awesome Apt in the Heart of Back Bay!

Perfect Location! Great Amenities Included!

Upscale Apt with everything you need!

Gorgeous Apt With Dedicated Flex-cation Office Space!

Beautiful, fully equipped, luxury condo!

Upscale Apt with everything you need!

Beautiful, fully equipped, luxury condo!

Spacious Back Bay Condo with Great Amenities!

Stylish Flex-cation Space in Back Bay!

Gorgeous Apt With Dedicated Flex-cation Office Space!

Upscale Apt with Private Work From Anywhere Office

Upscale Apt with Private Work From Anywhere Office

Bright Condo, Plenty of Room, Sleeps Upto 8

Outstanding 2 Bed Apt in Heart of Back Bay!

Spacious Back Bay Condo with Great Amenities!

Boston Back Bay Apt with fast wifi & great extras!

2 Bed with Work From Anywhere Office & Fast Wifi!

Awesome Apt in the Heart of Back Bay!

Cozy Studio with Great Wifi!

Authentic Brownstone Boston Studio!

Modern Studio in South End!

Bright Studio in Gorgeous Brownstone

Spacious Studio With Fast Wifi!

Large, Modern Studio!

Bright and Modern Luxury Studio

Great Value Studio in South End!

Cozy and Cute Value Studio!

Cute and Cozy Studio!

Gorgeous Studio with Bay Windows!

Cozy Studio with everything you need!

Modern Studio with Great Wifi and Amenities!

Great Value South End Studio!

Awesome studio in South End with wifi and parking

Bright Studio in Gorgeous Brownstone

Cute and Cozy Studio!

Awesome Studio with great amenities!

Modern Studio with Great Wifi and Amenities!

Spacious Studio With Fast Wifi!

Awesome studio in South End with wifi and parking

Cozy Studio with Great Wifi!

Authentic Brownstone Boston Studio!

Large, Modern Studio!

Cozy Studio with everything you need!

Great Value Studio in South End!

Gorgeous Studio with Bay Windows!

Bright and Modern Luxury Studio

Cozy and Cute Value Studio!

Great Value South End Studio!

Modern Studio in South End!