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Gloucester/Annisquam Getaway: Beach-Biking-Nature Trails-Kayaking

Gloucester, MA, USA
  • Apartment1245 sqft
  • Bedrooms3
  • Sleeps6
  • Bathrooms1
  • Half Baths0
  • Minimum Stay0 - 7 nights

3 Bedrooms, Sleeps 6, Close To Beach

Perfectly located turn of the century Bayview home is nestled between Annisquam Village and Lanesville… a short walk to Plum Cove Beach, 5 minute walk to the Greenbelt hiking trails in Dog Town, a mile from Halibut Point in Rockport and minutes away from some of the best kayaking in the area.

Here's a glimpse of beautiful Gloucester.


This Cape Ann getaway is a large updated open living space with one bedroom on the first floor (queen bed) and two bedrooms upstairs on the second floor: 1 queen and 2 twin bed (and views of the ocean).

Spacious open concept kitchen, living and dining area opens to the large private deck that offers ocean peeks. Home is light and airy with great livable space... the perfect getaway. The Willow Rest - just down the road - is a must for breakfast and lunch. The Market and Lobsta Land restaurants are minutes away for dinner on the water.

So much to do... boating, whale watching, fishing, swimming at breath taking beaches, and sea kayaking, biking, hiking, a vibrant art community and not to be missed sunsets over Ipswich Bay or on the beach at Plum Cove. Minutes to Rockport, and easily accessible by commuter rail from Boston. Boston & Salem MA -- less than an hour away.

Summer changeover day is Saturday.

Smoke and pet-free. Parking for two cars.

Check-in 3pm, Checkout 11am

Gloucester, founded in 1623, is America's oldest seaport. It is the quintessential New England town. Among the many maritime activities offered by Gloucester are: world class whale-watching expeditions, lighthouse tours, stunning destination beaches, the Gloucester Schooner Adventure, the Cape Ann Historical Museum, fishing and boating opportunities in abundance, the best seafood restaurants, and a lively nightlife rich with live music and theatre. Gloucester is also the home to National Geographic’s “Wicked Tuna”.

And.....Conde Nast says Gloucester and Cape Ann is a must see: http://www.cntraveler.com/galleries/2015-06-27/things-to-do-in-america-all-50-us-states/21


Regina Ryan

Member Since 2014
Response rate:
Response time:
within one hour
Calendar last updated:
Apr 17, 2018
About Regina Ryan

Jim's a sculptor and teaches in the arts department @ a Boston university. Regina is an entrepreneur who spends her time helping others get their businesses started.

Regina Ryan purchased this Apartment in 2013

Why Regina Ryan chose Gloucester

We love Gloucester and live here because of all the great and fun things to do, the people, and the serenity the area offers.

What makes this Apartment unique

Upon booking we will email you a unique electronic entry code for the front door lock for easy self check-in.


    • Internet
    • Air Conditioning
    • Heater
    • Satellite or Cable
    • Kids Welcome
    • Washer & Dryer
    • Parking
    • TV
    • No Smoking


      • 3 Bedrooms, Sleeps 6
      • Bedroom 1
        1 queen
      • Bedroom 2
        2 twin/ single
      • Bedroom 3
        1 queen
      • Linens supplied


      • 1 Bathroom
      • Bathroom 1
        toilet, combination tub/shower
      • Towels and basic toiletries provided

      Location Type

        • Beach View
        • Near The Ocean
        • Ocean View
        • Water View


            • Adventure
            • Away From It All
            • Family
            • Romantic
            • Sports & Activities


                • Guests provide their own meals


                    • Iron & Board
                    • Air Conditioning
                      AC in 1 bedroom. Skylights and fans in master bedroom and bedroom with twin beds.
                    • Hair Dryer
                    • Heating
                    • Internet
                    • Clothes Dryer
                    • Linens Provided
                    • Living Room
                      Open concept living room, dining room and kitchen that opens up onto deck with Weber grill.
                    • Parking
                      Parking on site for 2 cars.
                    • Towels Provided
                      Beach towels provided if requested.
                    • Washing Machine


                        • Coffee Maker
                        • Dishes & Utensils
                          Dinnerware (plates, silverware, mixing bowls, etc), glassware.
                        • Kitchen
                          Fully equipped kitchen with Calphalon cookware, blender, toaster, coffeemaker, panini press.
                        • Microwave
                        • Oven
                        • Pantry Items
                          Basic spices & herbs, filtered water, paper goods, soap, towels, napkins...
                        • Refrigerator
                        • Stove
                        • Toaster


                            • Dining
                            • Dining Area
                            • comfy seating for 6 people


                                • Books
                                • DVD Player
                                • Games
                                  A few games
                                • Satellite / Cable
                                  No pay-per-view
                                • Stereo
                                • Television
                                • Toys
                                  Some beach toys


                                    • Deck / Patio
                                      Private Deck with table, chairs and umbrella
                                    • Kayak / Canoe
                                      Kayaks can be rented in Lanesville just a couple of minutes away.
                                    • Outdoor Grill
                                      Weber grill.


                                        • Long-term Renters Welcome
                                        • wheelchair inaccessible


                                            • churches
                                            • cinemas
                                            • festivals
                                            • library
                                            • live theater
                                            • marina
                                            • museums
                                            • playground
                                            • restaurants

                                              Leisure Activities

                                                • photography
                                                • antiquing
                                                • bird watching
                                                • boating
                                                • horseback riding
                                                • paddle boating
                                                • beachcombing
                                                • scenic drives
                                                • shelling
                                                • shopping
                                                • walking
                                                • whale watching
                                                • wildlife viewing

                                                  Local Services & Businesses

                                                    • ATM/bank
                                                    • groceries
                                                    • hospital
                                                    • medical services

                                                      Sports & Adventure Activities

                                                        • pier fishing
                                                        • cycling
                                                        • equestrian events
                                                        • fishing
                                                        • hiking
                                                        • kayaking
                                                        • mountain biking
                                                        • deepsea fishing
                                                        • sailing
                                                        • scuba diving or snorkeling
                                                        • snorkeling
                                                        • snorkeling/diving
                                                        • sound/bay fishing
                                                        • swimming


                                                            • 100% refund if canceled 45 days before arrival date. Check-in 3pm, Checkout 11am.

                                                              11 Reviews


                                                              Latest reviews

                                                              Great place!

                                                              KRISTIN S.

                                                              This is the second time we stayed at this lovely, well-appointed VRBO. The unit is spacious and has great views of the ocean. My kids enjoyed collecting treasures at Hodgkins cove, right across the street (not the UMASS part, the little cove to the right which has public access). We stayed two times to visit with my sister who lives down the street and attend family weddings, but we're considering staying again just for fun, maybe in the summer. Highly recommend!


                                                              Edward B.

                                                              Beautiful home. Great location. Would definitely rent again!

                                                              GREAT PLACE!

                                                              James M.

                                                              Lovely apartment, recently redone, Great location near Plum Cove beach. Goucester is a fun place to kick back. Would rent this apartment again, in fact, we are planning our return...

                                                              Great time!

                                                              David C.

                                                              We had a dad's weekend away/50th birthday party, staying here while also doing a charter fishing trip. The untt was really nice (even better then the photos), the host was very friendly ad helpful (and even gave a bottle of wine to the birthday boy). The rental was clean and bright, the kitchen very functional, and in all it was a great experience. I'd highly recommend this rental!

                                                              A pleasant stay

                                                              Joseph M.

                                                              A very pleasant, clean apartment, well equipped and maintained. I would recommend this property. Also, a terrific lobster house two miles driving toward Rockport; and a sandy beach about a 1/2 mile away. (It would help to point which direction to the beach).

                                                              Two drawbacks: only one bathroom, and the upper bedroom is atop a narrow spiral staircase. This upper bedroom is suitable for kids.

                                                              But the first floor is spacious with a generous kitchen and eating area.

                                                              Overall a very good location.

                                                              Perfect Winter Break


                                                              The perfect winter break! With views of the ocean and access to the town and many walks, my family and I had a lovely weeklong stay in this spacious yet cozy home. Our host responded very promptly and the photos and description of the accommodation were extremely accurate. Everything was clean and comfortable.


                                                              Gloucester, MA, USA

                                                              Whale Watching, deep sea fishing, Home to "Wicked Tuna", Fishbox Derby, Farmers Markets, St. Perter's Festival, Harvard cruises. More info: http://gloucesterma.com/Attractions.cfm

                                                              Rates & Availability

                                                              Additional information about rental rates

                                                              Cleaning Fee
                                                              Damage Insurance
                                                              Tax Rate

                                                              Bookings made 45 days or less prior to Arrival must be paid in full when booking and are non-refundable 45 days prior to arrival. A cleaning service fee of $150 and damage insurance will be added to the quote. Check-in 3pm, Checkout 11am. Turnover day is Saturday during the summer season

                                                              11 Reviews
                                                              Wonderful 4.8/5
                                                              Enter dates for accurate pricing
                                                              For booking assistance, call 888-640-7927

                                                              Property # 609230