Annisquam River vacation rentals

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Top-rated vacation rentals in Annisquam River

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Guest favorite

Home in Gloucester

4.95 out of 5 average rating, 133 reviews

Views over Lobster Cove! Book spring weekends

Booking summer and fall 2025. Water views/access, sunsets above Lobster Cove on Washington St. Ideal for couple, NEW KING BED in master, queen in 2nd. Fast WiFi./TV. Not suitable for young children. Central A/C. 2nd fl unit large windows. Large living/dining/kitchen area. Comfy new mattresses, 100% cotton sheets,sound machines. Overlooks beautiful Lobster Cove and footbridge. Minutes walk to the village of Annisquam and Lighthouse Beach. Small deck. Swim/kayak out your door. Parking for one car

Top guest favorite

French doors open into a cozy living area where a sectional sofa is visible. A small green table with a bouquet of flowers sits in front, while sunlight illuminates the space. Outside, garden views reveal lounge chairs and vibrant flowers.

Guesthouse in Gloucester

4.96 out of 5 average rating, 269 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

Top guest favorite

Rocky coastal formations are depicted in the foreground, gently meeting the blue water. In the background, vibrant seaside buildings line the shore under a clear blue sky, offering an inviting view of the New England town's charming architecture.

Loft in Rockport

4.99 out of 5 average rating, 267 reviews

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

Top guest favorite

The image captures a serene waterfront view, featuring a calm blue harbor with boats docked along the pier. A stone wharf extends into the water, framed by lush greenery and a gravel area. Sunlight bathes the scene, creating a peaceful atmosphere.

Apartment in Rockport

4.98 out of 5 average rating, 186 reviews

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.

Guest favorite

A sunset view over the ocean is captured, with golden rays reflecting on the water's surface. Silhouettes of trees are visible in the foreground, along with a white deck railing outlining the space. The sky displays warm hues, transitioning from orange to soft gray.

Apartment in Gloucester

4.85 out of 5 average rating, 117 reviews

Amazing Ocean View In-Law Apt.

Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

Top guest favorite

The historic carriage house is presented in a charming turquoise color, surrounded by lush greenery and flowering plants. Tall windows provide ample natural light. A spacious yard is visible, framed by a low stone wall and iron fence.

Guesthouse in Rockport

4.99 out of 5 average rating, 112 reviews

Gingerbread House | Steps to Beach| Dog Friendly

Our historic carriage house in Downtown Rockport has everything you need for the perfect getaway, all year long! A two-minute walk to beaches, shops, galleries, parks, and playground. A peaceful family and pet-friendly space with all the amenities you need for a comfortable stay: laundry, full kitchen, queen sized bed with en-suite bathroom and a sun room that converts to an extra sleeping space perfect for kids. A 5 minute walk to the train for day trips to Salem, Gloucester, and Boston!

Guest favorite

A multi-story house features a prominent front porch, adorned with white railing and set against a grassy area. The roof showcases varied architectural styles, with prominent gables and dormer windows. Surrounding homes are visible, emphasizing the neighborhood setting.

Apartment in Gloucester

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.

Guest favorite

The exterior of a charming cottage is shown, featuring wooden siding painted in earthy tones. A decorative barrel planter with vibrant flowers is positioned at the base of the wall. Lush greenery climbs along the structure, with a white picket fence creating a welcoming boundary.

Loft in Gloucester

4.9 out of 5 average rating, 199 reviews

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

Guest favorite

A wooden deck overlooks marsh views, featuring tall bar stools and small tables arranged neatly. Guests can be seen enjoying their time at the water's edge as the sun sets, casting a warm glow across the scene.

Cottage in Essex

4.95 out of 5 average rating, 256 reviews

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.

Top guest favorite

A charming log cabin is nestled among trees, featuring a sloped roof covered in dark shingles. A wooden deck with steps leads to the entrance, while large windows allow natural light to illuminate the interior. The surrounding woodland is filled with natural greenery and rocks.

Cabin in Rockport

4.97 out of 5 average rating, 454 reviews

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.

Top guest favorite

A vine-covered deck features a small, round table surrounded by two woven chairs. Sunlight filters through the greenery, casting a soft glow on the wooden flooring. A potted plant adds a touch of nature to the inviting outdoor space.

Guest suite in Rockport

4.98 out of 5 average rating, 688 reviews

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.

Guest favorite

A stone path winds through a landscaped yard, bordered by vibrant pink peonies and greenery. A large tree provides shade, while neighboring properties are visible in the background, showcasing the charming outdoor space of the rental.

Condo in Gloucester

4.96 out of 5 average rating, 107 reviews

Luxurious beach house w/ harbor views & near beach

There isn't a better location on Cape Ann! Rocky Neck is the oldest art colony in the US. This luxurious 1br boasts ocean views & was updated w/ designer & custom features. Not only can you walk to the beach, there are amazing restaurants across the street and a wine & cheese bar featuring local art you can peruse while having a cocktail. Come and enjoy sunsets from the deck and everything else Gloucester has to offer!

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Popular amenities for Annisquam River vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Annisquam River

Top guest favorite

A charming private cottage is visible, featuring shingle siding and multiple windows. The entrance is framed by greenery, offering a serene environment. A small bench sits outside on the deck, which is accessed by glass doors that enhance natural light.

Guesthouse in Gloucester

4.93 out of 5 average rating, 75 reviews

Charming Guesthouse with Access to Private Beach

JaneRating, 5 stars1 week ago

We adored this adorable guest house. It was perfect for my husband and I as we vacationed in the North Shore. The location was central to all of the nearby towns and their place had everything we needed for our stay. It’s super cozy and quiet on their property. Their neighborhood is one of the cutest we saw during our travels too. If you like to walk, this is one of the most picturesque neighborhoods in Annisquam. The walk to the beach is right around the corner and it’s the cutest little walk. Cat and Lucy were extremely helpful with recommendations around the area and were very responsive to any questions we had. We saw Lucy during our stay and she was super sweet. If you’re lucky you’ll get a little visit from their dog, she’s adorable! We would definitely come back to stay again!!

Top guest favorite

A sandy beach is lined with colorful lounge chairs facing a tranquil water view. The sunset casts warm hues across the sky, reflecting softly on the calm water. In the background, a rocky shoreline leads to a distant structure, enhancing the serene beach atmosphere.

Home in Gloucester

4.96 out of 5 average rating, 28 reviews

Beach House on a Private Beach!

ToriRating, 5 stars6 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.

Top guest favorite

A two-story white Colonial house features a solar panel roof and a brick walkway leading to the entrance. The surrounding yard is well-maintained with green grass and shrubbery, complemented by trees that display fall foliage in the background.

Condo in Essex

5 out of 5 average rating, 32 reviews

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!

Guest favorite

A light-filled living room features large glass doors that open to the deck, offering ocean views. Comfortable seating includes a dark gray sofa and an armchair. A coffee table is centered on a textured area rug, with a flat-screen TV mounted on the wall opposite.

Apartment in Rockport

5 out of 5 average rating, 10 reviews

The Pearl, Apt. #2

RobertRating, 5 stars6 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.

Top guest favorite

A bright and airy open-concept living area features light-colored walls and warm wood flooring. A staircase with white railings leads to the upper level, while a cozy kitchen bar with seating for four is visible in the background. Natural light streams in through the nearby door.

Home in Rockport

5 out of 5 average rating, 32 reviews

Dog Friendly 2BR Home Walk to Beach+Bearskin Neck

NathalieRating, 5 stars3 weeks ago

This house has everything! Charming location, easy layout, all new appliances, gorgeous linens, and it was spotlessly clean! You can see the ocean from one side! Easy walk to all of the cute things in Rockport. Rachel was a wonderful responsive host, and the neighbors were nice. We loved everything about it! Thanks Rachel!

Superhost

A sandy beach stretches out under a clear blue sky, with gentle waves lapping at the shore. In the background, several houses are positioned on a rocky outcrop, showcasing a serene seaside environment.

Apartment in Gloucester

4.85 out of 5 average rating, 99 reviews

Long Beach Suites: Steps Away From Surf!

SamRating, 5 stars6 days ago

This place was perfect for the 1 night stay that I needed while in the area for an event. Exactly as described and had everything I needed. Lucas was a great host and provided plenty of instructions & information beforehand with multiple reminders as my stay approached. I would stay here again.

Top guest favorite