Holiday rentals in Annisquam River

Guest house in Gloucester

4.96 out of 5 average rating, 268 reviews

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

4.99 out of 5 average rating, 267 reviews

Loft in Rockport

Chic Downtown Loft ☆ Private Parking ☆ Ocean View

Enjoy the coastal and seaside views from the renovated and bright "jewel" located in the charming seaside New England town of Rockport on Cape Ann. The loft is centrally located is literally steps to the beaches, the Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu. 1-min walk to Bearskin Neck & Motif No.1 5-min walk to Front Beach + easy access to many others 8-min drive to Halibut Point Park 25-min drive to Salem 1-hour drive to Boston 15-min walk MBTA Train Station

4.98 out of 5 average rating, 185 reviews

Flat in Rockport

Waterfront Escape! In-town with onsite parking

Brand new waterfront apartment in historic home with onsite parking & private entrance in the heart of town. Views and access to historic harbor from private deck. Beaches, galleries, restaurants, coffee shops, live music and shopping on Bearskin Neck are steps away. Features full kitchen and bathroom with new applicances and fixtures. Living room has a loveseat, swivel chair, dining table, coffee table, roku TV, games, puzzles & books. Kitchen has a fridge, stove, oven, microwave and Keurig.

4.96 out of 5 average rating, 157 reviews

Apartment in Gloucester

KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN

Looking for the perfect Gloucester retreat for your group or family? Look no further than this spacious and inviting 2-bedroom unit, ideal for families and groups seeking comfort, style, and ample room to relax. Step inside and be greeted by a bright and spacious living area, perfect for gathering together after a day of exploring all that Gloucester has to offer. With its comfortable furnishings and modern amenities, this unit is designed to provide you with the ultimate vacation experience.

4.98 out of 5 average rating, 101 reviews

Apartment in Rockport

1 Bedroom 1 Bath Waterview Downtown w/ Parking

Steps to ocean, steps to restaurants and shops. Quiet and quaint. Enjoy this centrally-located unit with all the town of Rockport has to offer right out the front door. Clean and fresh, with ocean views from the kitchen and living room. Unit has been renovated and updated with fresh paint, new appliances, new mattress and new sleeper sofa for guests. Enjoy the town shops, restaurants, sights, and beach all with a short scenic walk. This is Main Street, USA. Desirable Downtown Parking spot.

4.97 out of 5 average rating, 117 reviews

Beautifully remodeled unit in heart of Gloucester

Enjoy your stay in the heart of Gloucester close to everything this great town has to offer. This unit was completely remodeled in 2022. Two shorts blocks from Main Street in Gloucester and all of its wonderful restaurants and shops. Three blocks from the Beauport Hotel - perfect for wedding guests not staying at that location. This unit has new floors, countertops, appliances and fixtures and is freshly painted (no VOC paint). You will love this unit and location for your visit.

4.9 out of 5 average rating, 199 reviews

Loft in Gloucester

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2024! We look forward to you visiting RockyNeck in Gloucester. You will be sure to enjoy various special activities and events this summer and fall. We are located in the "quiet end", on a private residential dead end street in a historic artist colony . Nearby public transportation, Audubon sites, cultural events, the Gloucester Stage Co and beaches . Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV

4.95 out of 5 average rating, 256 reviews

Cottage in Essex

French Flair "Pied a Terre" Cottage on the Marsh

Sunny cottage with marsh views, under 5 minute walk to town. Eat on the water in one of the many village restaurants, rent a kayak or paddle board. Go "down river" like a local! Shop the world renowned antique stores or enjoy the local beaches. There are many unique places to visit in Gloucester, Manchester, Rockport, Ipswich, Salem and of course Boston. There is a Visitor Manual for your convenience and we would be happy to answer questions that you might have.

4.97 out of 5 average rating, 454 reviews

Cabin in Rockport

The Solar Powered Dogtown Cabin at Applecart Farm

Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

4.95 out of 5 average rating, 108 reviews

Flat in Rockport

Downtown Rockport|King Bed w/Parking|Walk to Train

• Newly remodeled and professionally furnished space! • Steps to Beaches, Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu • Private off street parking spot for 2 cars • High Speed Wi-Fi and AC • 10 minute walk from commuter rail to Boston • Smart TV equipped to stream all your favorites • Fully stocked and renovated kitchen • Comfortable KING size memory foam bed • Convenient EV charging right across the street!

4.98 out of 5 average rating, 688 reviews

Guest suite in Rockport

Halibut Point State Park. Nature Lovers Retreat

"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.

4.96 out of 5 average rating, 142 reviews

The Gilbert: 1-Bed downtown suite, walk to beach.

Come stay in Gloucester’s historic downtown district, in St. Peter’s Square, just one block from Pavilion Beach, Stacey Boulevard and the historic West End of Main Street. The Gilbert sleeps two (up to 3 with an air mattress). A perfect getaway for those in love with history and seaside living. The unit has a private entrance, king sized bed, kitchenette and private bath.

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Other great holiday rentals in Annisquam River

4.99 out of 5 average rating, 74 reviews

Ocean Breeze / 8 min walk to Beach

HeatherRating, 5 starstoday

My daughter and I had a great time. It was very peaceful and quiet and a short walk to the beach. Thank you for allowing us to stay in your beautiful apartment.

4.96 out of 5 average rating, 28 reviews

Home in Gloucester

Beach House on a Private Beach!

ToriRating, 5 stars5 days ago

Oh my goodness. This place was a DREAM. Such a beautiful home with a view you can’t top. My husband and I stayed with our children and two friends for an east coast summer getaway and we could not have found a better place. Awesome setup, view, and Gaby could not have been more helpful. We would love to stay here again.

5 out of 5 average rating, 32 reviews

Apartment in Essex

Marshside one-bedroom with stunning view

KarenRating, 5 stars2 weeks ago

Mark's place was outstanding. It was spacious, comfortable and well-equipped. We chose the location because of the local views (the marsh is so beautiful, and it did not disappoint!) and because of the excellent reviews, and it met all our hopes and expectations. As a fellow Airbnb host who wants a very clean place for my own guests and when I travel, I think this was the cleanest place I've every stayed. It was truly spotless, which was so lovely. Mark was responsive and helpful when we had a question. The bed was comfortable (albeit tall--a short person might need a boost up!), there was so much closet room, and overall plenty of space to spread out. The kitchen was bright & well outfitted. We had a wonderful time, even though we arrived in the middle of an unusual late-May Nor'easter. We enjoyed the local restaurants and cute Mayflour bakery, and used Mark's guide book for choosing a beach. We very much hope to come back! Thank you Mark for your kind hospitality!

Home in Gloucester

5 out of 5 average rating, 3 reviews

Buoy 23 Vacation Home Rentals

BrandonRating, 5 stars7 months ago

We had an awesome stay at Allison’s house. Communication with Allison was effortless and easy. The location was private and serene right on the ocean. The house was stocked with everything you needed for a comfortable stay. There was a private dock just steps outside in the backyard. We had a very relaxing and peaceful stay and will definitely be back.

5 out of 5 average rating, 10 reviews

Flat in Rockport

The Pearl, Apt. #2

RobertRating, 5 stars5 days ago

Very nice apartment with a wonderful balcony with comfy chairs overlooking the gorgeous bay, with sandy beach and rocky coast. The apartment was clean and comfortable with nice amenities. Great kitchen and bathrooms. Beds are comfortable and extra blankets are in the closet. Plenty of storage for clothing. The upstairs bedroom area was up a ladder which precludes small children. It was okay for our 5 year old but not for the 3 year old. The town is lovely and the center of town just 4 or 5 minutes away on foot. Beach access is just a minute away. Mary was a wonderfiul host and helpful. This is one of the lovliest AirBNBs we've stayed in and highly recommended.

5 out of 5 average rating, 40 reviews

Blue Magnolia

KimRating, 5 stars6 days ago

We stayed at Blue Magnolia to celebrate a friend’s birthday. We were a group of 5 women and had plenty of room. It was so comfortable and clean. Michael was incredibly helpful with directions and answered all questions quickly. My group would stay again. We loved our stay.