Gloucester – Annisquam Rentals Make Great Destinations

When you are looking for a great way to spend time on the northern Massachusetts shore, Gloucester – Annisquam rentals are excellent choices. Rentals in Gloucester, MA offer the convenience of being near downtown Gloucester while still remaining just outside the city.

Enjoy Quiet Relaxation with Gloucester – Annisquam Rentals


If you are seeking a quiet Gloucester rental, then Annisquam is the perfect destination for your vacation. This Gloucester neighborhood is mostly residential and offers few commercial businesses. The area does offer a marina, yacht club, restaurant, and the famed Annisquam lighthouse. The lighthouse has stood since 1801 and the beach on which it sits is known as Lighthouse Beach. There are many Annisquam rentals near Gloucester, MA that offer beautiful views of the historic lighthouse.

A Gloucester Rental Offers a Great Way to See a Beautiful City


Gloucester, Massachusetts is a wonderful city that offers many places for travelers to explore. Take in the beautiful city hall building, which is only one example of the city's famous and significant architecture. Gloucester – Annisquam rentals provide guests with easy access to such attractions as the Man at the Wheel statue as well as the many art and sculpture museums. The city has been mentioned in many famed films and books, and a brief tour of the city helps show visitors exactly why. A Gloucester rental makes a perfect accommodation for travelers looking to see the historic area and guests lucky enough to come during the St. Peter's Festival will find that the city is filled with culture.

Rentals in Gloucester, MA Also Offer Outdoor Activity and Beautiful Surroundings


Gloucester – Annisquam rentals give guests the chance to explore the Massachusetts Bay as well as the Atlantic Ocean. The location is ideal for boaters and offers many options for fishing, swimming, and sailing.

When you decide to spend your vacation in a Gloucester rental, you will find yourself in a beautiful accommodation that features full furnishings and many amenities. Rentals in Gloucester, MA are available to suit any size family or group and offer wonderful accommodations for travelers looking to relax and enjoy the beauty of Eastern Massachusetts. Search today!

Increase your search options for vacation rentals in North Shore Massachusetts by checking out additional vacation properties, such as vacation homes in Marblehead MA, Plum Island beach rentals, Rockport Massachusetts cottage rental, or Lodging in Salisbury Beach Massachusetts.



Gloucester Annisquam MA Apartment Rental

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Beautiful home for rent on Wingaersheek Beach in the private section

— Property 195397
Gloucester - Annisquam house rental - Wingaersheek Beach Sunset
6 Bedrooms, Sleeps 15,
House, 3 Bathrooms, beach, waterfront, tennis court
Rates - per property (USD)
$2,000 - $4,200/week
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Historic Home Located on Scenic Eastern Point

— Property 194764
Gloucester - Annisquam apartment rental
1 Bedroom, Sleeps 2,
Apartment, 1 Bathroom, beach, near the ocean, air-conditioning
Rates - per property (USD)
$175/night
$1,100/week
$3,500/month
Calendar Updated Nov 29 2009

Property Review

My wife and I just stayed at this house and had a wonderful weekend. The owners are great and very accomodating. The apartment is spacious and well appointed. We particularly enjoyed the fact that...
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On the Cove - Beautiful Apartment Directly on Lanes Cove

— Property 122459
Gloucester - Annisquam apartment rental - View of the sunset taken from the property
1 Bedroom, Sleeps 4,
Apartment, 1 Bathroom, near the ocean, village, internet access
Calendar Updated Nov 24 2009

Property Review

Thank you both for giving us the opportunity to have such a great time on the cove! In the morning we loved to have breakfast on the patio with an excellent ocean view. We used to live in that...
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New England Cape on Folly Point near village center in Seaside Lanesville

— Property 136921
Gloucester - Annisquam house rental - 10 Folly Point
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, 1 Half Bath, beach, village, garden
Rates - per property (USD)
$1,800 - $2,000/week
Calendar Updated Nov 23 2009

Property Review

We recently spent the Christmas holiday at 10 folly point and we were completely charmed. The home has a comfortable but elegant homey feel with really high quality furniture and fully stocked...
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Charming Private Annisquam Cottage - Diamond Cove- Dogs OK

— Property 238689
Gloucester - Annisquam cottage rental
4 Bedrooms, Sleeps 9,
Cottage, 2 Bathrooms, 1 Half Bath, beach, near the ocean, garden
Rates - per property (USD)
$1,300 - $1,900/week
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Annisquam Waterfront: Ocean, Beach & Sunsets

— Property 114626
Gloucester - Annisquam house rental - Beautiful Waterfront
3 Bedrooms, Sleeps 7,
House, 3 Bathrooms, beach, waterfront, pets considered
Calendar Updated Nov 23 2009

Property Review

Being in this home was such a wonderful way to spend the last leg of our East Coast family vacation. We traveled with our toddler and pre-teen sons and they both had room to roam in this home. ...
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Ledge House near ocean in Gloucester, MA

— Property 237496
Gloucester - Annisquam house rental - Ledge House
4 Bedrooms, Sleeps 6,
House, 1 Bathroom, 1 Half Bath, beach, near the ocean, tennis court
Rates - per property (USD)
$1,500/week
$1,200/month
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Panoramic Water View

— Property 113373
Gloucester - Annisquam house rental - Hovey House
7 Bedrooms, Sleeps 16,
House, 5 Bathrooms, downtown, waterfront, garden
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Quiet, modern apartment on Good Harbor Beach (Gloucester, MA)

— Property 113120
Gloucester - Annisquam apartment rental
2 Bedrooms, Sleeps 6,
Apartment, 1 Bathroom, beach, near the ocean, garden
Rates - per property (USD)
$1,250/week
$1,150/month
Calendar Updated Nov 20 2009

Property Review

The location was perfect. The property was clean and updated
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Wingaersheek Luxury Beach Front Home- Private Sect- Year Round- 5 BR- 2 1/2 Bath

— Property 170522
Gloucester - Annisquam house rental - Beach view from upper deck
5 Bedrooms, Sleeps 15,
House, 2 Bathrooms, 1 Half Bath, beach, waterfront, garden
Rates - per property (USD)
$2,500 - $4,800/week
Calendar Updated Nov 18 2009

Property Review

We have gone to many beach houses. The Outer Banks, Cape Cod, and RI. Our extended families included an 8 mth old, 3 year old, 5 and 6 year olds, along with two 14 year olds, 18 and 21 year olds...
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Wingaersheek Beach (Private Section) Bungalow -

— Property 108307
Gloucester - Annisquam house rental
3 Bedrooms, Sleeps 10,
House, 1 Bathroom, beach, near the ocean, DVD
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New, Trendy and Affordable for Weekly Vacations

— Property 246498
Gloucester - Annisquam apartment rental - View of gardens & the ocean from the private deck
1 Bedroom, Sleeps 4,
Apartment, 1 Bathroom, near the ocean, town, garden
Rates - per property (USD)
$600 - $850/week
$800/month
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Fabulous for family vacations and couples & friends getaway

— Property 207240
Gloucester - Annisquam house rental - converted Carriage House
2 Bedrooms, Sleeps 8,
House, 2 Bathrooms, 1 Half Bath, town, waterfront, jacuzzi
Rates - per property (USD)
$1,200 - $1,700/week
$1,200/month
Calendar Updated Nov 13 2009

Property Review

Wow, what a gem this vacation home is, my family of 4 loved it. Everything is exceptionally well kept and all essentials are there for your use. My 2 kids were thrilled with their room and...
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Cape Ann, Annisquam 4 bedroom house with panoramic ocean views from every room.

— Property 134469
Gloucester - Annisquam house rental - West Facing Porch - Ipswich Bay View
4 Bedrooms, Sleeps 11,
House, 1 Bathroom, 1 Half Bath, beach, near the ocean, garden
Rates - per property (USD)
$1,500 - $2,900/week
Calendar Updated Nov 11 2009

Property Review

Fabulous old beach house, nicely updated while retaining all the charm. The porch is divine! Would liked to have stayed for the whole summer. You will not be disappointed!
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Idyllic ocean-front Gloucester cottage

— Property 182967
Gloucester - Annisquam cottage rental - Sunset from porch
2 Bedrooms, Sleeps 7,
Cottage, 2 Bathrooms, beach, waterfront, garden
Rates - per property (USD)
$1,800/week
Calendar Updated Nov 11 2009

Property Review

We enjoyed our week at Endless Summer. It's a nice quiet location, with a nice view but not that far of a drive to look around and explore. The kitchen was well equipped if you like to cook. The...
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Luxury 1900's romantic retreat steps from the beach - Book Now for Fall!!

— Property 140506
Gloucester - Annisquam cottage rental - Spectacular Sunsets at Plum Cove Beach!
1 Bedroom, Sleeps 2,
Cottage, 1 Bathroom, beach, near the ocean, garden
Rates - per property (USD)
$1,100/month
Calendar Updated Nov 10 2009

Property Review

Say "goodbye" to false advertising with the Plum Cove Cottage. It is everything they say it is and more! Wonderful amenities, location, scenery, and activities within easy walking and driving...
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Charming 1900's historic, colonial escape just steps from the beach

— Property 238293
Gloucester - Annisquam house rental - Spectacular sunsets at Plum Cove Beach
2 Bedrooms, Sleeps 4,
House, 1 Bathroom, beach, near the ocean, air-conditioning
Rates - per property (USD)
$1,500/month
Calendar Updated Nov 9 2009

Property Review

Upon arrival, we could not enter the rental cottage according to the instructions (lockbox codes) provided by the proprietor. We simply flipped a latch on a rickety side gate (the top of the post...
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Rocky Neck Studio Apartment in Gloucester

— Property 264908
Gloucester - Annisquam studio rental - Area View
Studio, Sleeps 2,
Studio, 1 Bathroom, near the ocean, town, internet access
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Water front Home with 'The Views'

— Property 177725
Gloucester - Annisquam house rental - Easterly Water View towards Annisquam
6 Bedrooms, Sleeps 12,
House, 2 Bathrooms, 1 Half Bath, near the ocean, waterfront, pets considered
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Water Views overlooking Gloucester's inner harbor

— Property 192597
Gloucester - Annisquam house rental - Sunporch overlooking harbor
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, 1 Half Bath, town, waterfront, jacuzzi
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Stunning Studio with Deck Overlooking Scenic Harbor

— Property 120975
Gloucester - Annisquam studio rental - Dining Al Fresco
1 Bedroom, Sleeps 2,
Studio, 1 Bathroom, beach, waterfront, air-conditioning
Rates - per property (USD)
$575 - $750/week
$775/month
Calendar Updated Oct 22 2009

Property Review

Linda has thought of everything when equipping this lovely apartment. Everything in the listing was there, and more. It made our stay very comfortable, and provided a place for my husband to...
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Coastal Weekly (Sat to Sat) Rental - by Beaches/Ocean, Cozy, Cute

— Property 187283
Gloucester - Annisquam apartment rental - Eastern Point Lighthouse & Breakwater - Few Miles
1 Bedroom, Sleeps 4,
Apartment, 1 Bathroom, beach, near the ocean, garden
Rates - per property (USD)
$525 - $840/week
$875 - $3,150/month
Calendar Updated Oct 15 2009

Property Review

Earlier this summer in June, I was visting family in gloucester and we picked this coastal retreat because it was affordable, and close to the ocean and beaches. We loved it. From the comfy bed...
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Beachfront escape

— Property 153899
Gloucester - Annisquam apartment rental - Enjoy views and ocean breezes from your deck
1 Bedroom, Sleeps 4,
Apartment, 1 Bathroom, beach, waterfront, garden
Rates - per property (USD)
$150 - $175/night
$400 - $1,000/week
$1,000/month
Calendar Updated Oct 15 2009

Property Review

Beautiful sunsets viewed from deck. Enjoyed birdwatching on the beach. Close to art colony and galleries on Rocky Neck. Gorgeous English gardens and flower boxes abound. Short walk to Niles...
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Gorgeous Gloucester Harbor views from 2nd floor two bedroom condo.

— Property 238327
Gloucester - Annisquam condo rental - Ext. of building
2 Bedrooms, Sleeps 5,
Condo, 1 Bathroom, downtown, near the ocean, garden
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Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester)

— Property 177143
Gloucester - Annisquam house rental - Front of House
3 Bedrooms, Sleeps 8,
House, 1 Bathroom, 1 Half Bath, beach, near the ocean, balcony
Rates - per property (USD)
$225 - $1,800/night
$1,200 - $1,800/week
$2,000 - $6,000/month
Calendar Updated Oct 13 2009

Property Review

We visited this vacation home in mid April, 2008. All of us were very comfortable from the time we first opened the door. It was clean and cozy. Having a family room and a livingroom was great...
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Charming 1860's Home Close to Plum Cove Beach

— Property 133898
Gloucester - Annisquam house rental - Corner of Bayview and Washington
3 Bedrooms, Sleeps 5,
House, 1 Bathroom, 1 Half Bath, beach, near the ocean, internet access
Rates - per property (USD)
$100 - $125/night
$700 - $1,200/week
Calendar Updated Oct 8 2009

Property Review

We came in october for halloween in salem. The house was as nice as the pictures. It was close to rockport where we took the train to salem and boston and just walked around from there so did not...
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Oceanfront, Wall-to-Wall windows with stunning views, walk to beach!

— Property 163333
Gloucester - Annisquam house rental - Enjoy the views of Salt Island from your deck!
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, beach, waterfront, balcony
Rates - per property (USD)
$1,000 - $3,500/week
Accepts Online Payments
Calendar Updated Sep 30 2009

Property Review

My wife, two teenage daughters and I just spent a week the end of May '09 at Four Winds. The house was everything the owner said it was and more. Very clean and spacious with magnificent views. ...
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Direct Waterfront, Gateway Cottage!

— Property 152300
Gloucester - Annisquam cottage rental - View from Master Bedroom
1 Bedroom, Sleeps 6,
Cottage, 2 Bathrooms, 1 Half Bath, waterfront, jacuzzi
Rates - per property (USD)
$1,400 - $1,875/week
$3,000 - $6,500/month
Calendar Updated Oct 1 2009

Property Review

What a delightful property. My husband and I just returned from a week at Gateway Cottage. We have visited Cape Cod several times in the past and decided to try a new area we had not been to...
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Beautiful Condo close to beaches, downtown and Stage Fort Park!

— Property 226721
Gloucester - Annisquam condo rental - View
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, downtown, near the ocean, garden
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Wheeler's Point! Annisquam Waterfront Getaway with Tidal Dock!

— Property 192566
Gloucester - Annisquam house rental - Alt. view of dock/float
2 Bedrooms, Sleeps 6,
House, 1 Bathroom, 1 Half Bath, river, waterfront, balcony