Vacation Rentals in Gloucester - Annisquam

Experience spectacular sunsets, relax on your private patio, launch your kayak from the back yard, peaceful walks along beautiful Lanes Cove where you can buy...

This gracious shingle-style house sits securely atop a rocky promontory overlooking picturesque Diamond Cove, in Annisquam. Our house has postcard seascape views...

Beautiful, newer home in natural setting. Tastefully decorated and fully furnished. Tons of closet space, two full baths, master bath shower is family-size with 2...

Charming 3 bedroom Cape Cod style house for rent in the Lanesville section of Gloucester, available immediately. Situated at the end of a cul-de-sac, the house has...

Filled with light and relaxing open-space on two levels, both with den/family-room amenities (TV and DVD/VCR), this comfortable house offers beautiful views of...

This lovely, tastefully decorated 3 BR home is 4/10 mile from the soft sands of spectacular Good Harbor Beach. Whether taking a morning walk or packing a cooler and...

Relax at the scenic New England coastline while residing at a new Victorian vacation home. This comfortable home offers an open living/dining/kitchen area with 2...

Spacious, sunny, private, luxury retreat with postcard views overlooking scenic marina and tidal river just minutes from the famous fishing port of Gloucester (as...

*Winter rental *available 10/1, 2007 through 5/1, 2008* Summer, June/July/August 2008 - Gorgeous Wingearsheek Beach Front Home, private section.***Wonderful year...

A simple, fun and affordable ideal summer retreat by the sea for you and your family. Gloucester’s best fishing, running, biking, ocean swimming, windsurfing, Scuba...

This quaint 1900's cottage was completely renovated in 2006. It has seasonal ocean views and Plum Cove beach is just 500 ft away!

As cozy and convenient as it is affordable, this simple and bright efficiency suite is located within a few minutes walk and drive of Gloucester's Back Shore and...

Nestled on a hillside overlooking Gloucester's scenic harbor... enjoy magical sunsets, dining al fresco, twinkling harbor lights, and warm summer winds from the deck...

Second floor apartment on small beach at entrance to historic Rocky Neck art colony. Spectacular ocean views. Sit on your waterfront deck; watch sea birds in the...

Prime Summer weeks available !!! Classic New England clapboard but thoroughly modern in its appointments. This spacious 4000 square foot home offers 5 comfortable...

Sun-filled cottage nestled up to beautiful Stage Fort Park in Gloucester. House is 1160 sq ft, 1st flr consists of one bedroom, one full bath, eat-in kitchen,...

Enjoy the beauty of Cape Ann. Pristine home situated on a private country road. This neighborhood is great for families or some much needed rejuvenation.

Fantastic sunsets! Enjoy waterfront living with beautiful views from every room. Swim, kayak, fish, clam, walk, bike or just relax from your own deck and dock.

Nestled in the heart of downtown, Julietta House is just footsteps from Gloucester Harbor, Main St. and the Train to Boston. Walk to waterfront, galleries,...

Endless Summer is a beautiful ocean-front cottage in a quiet Lanesville neighborhood. The beach is large, flat rocks typical of the Northern New England coast.