Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Condos
Cottages
Estates
Homes
Studios
Townhomes
Villas
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Farmhouses
Hotels
Lodges
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Gloucester - Annisquam Vacation Home Rentals(85)

85 Results
4 - 7 night minimum stay
  • 7 BR,
  • 3 BA,
  • Sleeps 16
    (18)
    4 - 7 night minimum stay
    • 3 BR,
    • 2 BA,
    • 1 HF BA,
    • Sleeps 6
      (40)
      2 - 7 night minimum stay
      • 5 BR,
      • 2 BA,
      • 1 HF BA,
      • Sleeps 14
        (5)
        2 - 7 night minimum stay
        • 6 BR,
        • 3 BA,
        • Sleeps 15
          (5)
          2 - 7 night minimum stay
          • 5 BR,
          • 3 BA,
          • Sleeps 14
            Book it Now!
            • 1 BR,
            • 1 BA,
            • Sleeps 4
              Book it Now!
              14 night minimum stay
              • 4 BR,
              • 2 BA,
              • Sleeps 8
                • 4 BR,
                • 2 BA,
                • Sleeps 12
                  (3)
                  14 night minimum stay
                  • 4 BR,
                  • 2 BA,
                  • 1 HF BA,
                  • Sleeps 9
                    3 night minimum stay
                    • 5 BR,
                    • 3 BA,
                    • Sleeps 10
                      1 Review
                      7 night minimum stay
                      • 2 BR,
                      • 1 BA,
                      • 1 HF BA,
                      • Sleeps 4
                        2 Reviews
                        1 - 31 night minimum stay
                        • 2 BR,
                        • 1 BA,
                        • Sleeps 4
                          (6)
                          7 night minimum stay
                          • 4 BR,
                          • 1 BA,
                          • Sleeps 7
                            (4)
                            7 night minimum stay
                            • 2 BR,
                            • 1 BA,
                            • Sleeps 5
                              (19)
                              Book it Now!
                              2 - 7 night minimum stay
                              • 5 BR,
                              • 2 BA,
                              • Sleeps 13
                                (7)
                                Book it Now!
                                7 night minimum stay
                                • 4 BR,
                                • 2 BA,
                                • Sleeps 9
                                  Book it Now!
                                  1 - 2 night minimum stay
                                  • 4 BR,
                                  • 3 BA,
                                  • 1 HF BA,
                                  • Sleeps 8
                                    2 - 90 night minimum stay
                                    • 5 BR,
                                    • 3 BA,
                                    • Sleeps 10
                                      (5)
                                      $327 - $1,600
                                      per week
                                      7 - 30 night minimum stay
                                      • 2 BR,
                                      • 2 BA,
                                      • 1 HF BA,
                                      • Sleeps 6
                                        4 - 7 night minimum stay
                                        • 3 BR,
                                        • 2 BA,
                                        • 1 HF BA,
                                        • Sleeps 8
                                          2 Reviews
                                          7 night minimum stay
                                          • 4 BR,
                                          • 2 BA,
                                          • Sleeps 11
                                            (9)
                                            • 5 BR,
                                            • 2 BA,
                                            • 1 HF BA,
                                            • Sleeps 9
                                              Book it Now!
                                              • 2 BR,
                                              • 1 BA,
                                              • Sleeps 4
                                                Book it Now!
                                                3 - 7 night minimum stay
                                                • 4 BR,
                                                • 2 BA,
                                                • 1 HF BA,
                                                • Sleeps 8
                                                  (6)
                                                  Book it Now!
                                                  3 - 7 night minimum stay
                                                  • 3 BR,
                                                  • 1 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 8
                                                    (3)
                                                    • 3 BR,
                                                    • 2 BA,
                                                    • Sleeps 8
                                                      2 Reviews
                                                      • 3 BR,
                                                      • 1 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 9
                                                        1 Review
                                                        1 - 7 night minimum stay
                                                        • 2 BR,
                                                        • 2 BA,
                                                        • Sleeps 4
                                                          (6)
                                                          7 night minimum stay
                                                          • 4 BR,
                                                          • 1 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 10
                                                            (6)
                                                            7 - 30 night minimum stay
                                                            • 4 BR,
                                                            • 1 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 6
                                                              (6)
                                                              Advertisement
                                                               

                                                              Recent Gloucester - Annisquam Reviews

                                                              Charming house, relaxing weekend

                                                              5 of 5
                                                              This is a unique house with lots of space, comfortable and unique character, set aside in a relaxing patch of woods. Just down the street from beautiful coastline/state park and an amazing lobster shack, short drive from lots of beautiful beaches. We met a few other couples here for a long weekend and had a wonderful time. At one point we lost hot water, and Kathy was very responsive, showed up right away to arrange for a handyman to come by that same day and fixed it. Highly recommended and we would certainly return.
                                                              • Submitted: Sep 8, 2014
                                                              • Stayed: Aug 2014

                                                              Great Place and Great Location

                                                              5 of 5
                                                              A nice big yard for the kids and dogs to play, a warm/homey feel inside, very accommodating owners, and the proximity to a great beach made it the perfect place to stay. We look forward to staying here in the future.
                                                              • Submitted: Sep 5, 2014
                                                              • Stayed: Jul 2014

                                                              Wonderful home!

                                                              5 of 5
                                                              My husband, son and I stayed here with another couple and their daughter for a week in August. The house was very clean and comfortable with plenty of places to lounge around. The kitchen was well-equipped and we were able to cook everything from clam chowder to baked ziti (there are also plenty of lobster-sized pots). My son has autism and tends to get into everything but the house was very safe for children, and far enough from other homes that we didn't need to worry about noise. We used the golf cart a lot, both to bring gear down to the beach and just to tool around - the kids loved it. After the kids went to bed the adults were able to sit out on the screened-in back porch, which was also great. Pete was an absolute delight to work with and I wouldn't hesitate to contact him again. Great vacation.
                                                              • Submitted: Aug 29, 2014
                                                              • Stayed: Aug 2014