Vacation rentals in Annisquam River

4.96 out of 5 average rating, 269 reviews

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

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

4.89 out of 5 average rating, 224 reviews

A serene harbor scene is captured, featuring a variety of boats docked on calm waters. Colorful vessels line the foreground, while charming buildings and fishing equipment can be seen in the background against a clear blue sky.

Apartment in Rockport

Charming Rockport Studio Apt

10 min walk to Town, Bearskin Neck, Tuna Wharf & Rockport's world famous Motiff #1. Old Garden Beach 5 min walk. 15 min walk to Front Beach & Rockport Train Station (Rockport Line from Boston (North Station). Studio Apt has all amenities to cook yummy meals, cozy bed, wash clothes, WIFI, Cable TV in quiet peaceful neighborhood w/ off-street parking. Hardwood floors, high ceilings, lots of windows make this studio apartment an ideal launchpad from which to explore Rockport, Gloucester & Cape Ann.

4.98 out of 5 average rating, 186 reviews

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

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.

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.

4.96 out of 5 average rating, 118 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

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

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2025! 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, 257 reviews

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

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.

4.94 out of 5 average rating, 124 reviews

Guest suite in Rockport

The Perfect Get-Away Suite | Near Shops & Beaches

Everything in this suite is new, clean, tidy and modern. There is plenty of natural light and privacy blinds. There is Wifi and HD Cable with Netflix, Prime and other platforms. There is also a kitchenette in the unit with sink, small refrigerator, microwave oven and coffee maker. The house sits on a third acre of land and is fenced in from the road. We are a ten minute walk to the beach and shopping area, and the train station is located only two blocks away.

4.97 out of 5 average rating, 454 reviews

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

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, 109 reviews

An aerial view captures the serene coastline, with sandy beach gently merging into clear blue waters. Quaint homes and greenery line the shore, showcasing a tranquil atmosphere. The surrounding hills create a natural backdrop, enhancing the peaceful coastal setting.

Apartment 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, 690 reviews

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

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.

4.87 out of 5 average rating, 214 reviews

The image depicts a calm harbor filled with various boats, including fishing and recreational vessels. Blue waters reflect the clear sky, while a red building and harbor structures are visible in the background, providing a hint of the coastal setting.

Guest suite in Rockport

Charming Studio in the Pines

This is a first floor, above ground, garden apartment in a private home and is located in a quiet neighborhood with the backyard nestled in the woods, just out side your sliding door. Flower gardens and bird feeders adds ambiance for relaxing in a private setting. The studio offers a kitchenette, dining nook, a full bathroom, a queen bed, plus a sofa. Also available is CableTV, Netflix and Wi Fi.

A charming entrance features a dark door, framed by white trim and an oval window. Potted flowers in shades of pink adorn either side of the doorway. A well-maintained walkway, constructed with cobblestones, leads to the entrance, surrounded by green shrubs and trees.

4.97 out of 5 average rating, 144 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 vacation rentals in Annisquam River

4.94 out of 5 average rating, 77 reviews

A warm wooden interior features a spacious bed adorned with a quilt. Two windows on either side allow natural light to illuminate the space. Light wooden paneling and sloped ceilings create an inviting atmosphere. A small floral arrangement sits on the nightstand.

Guesthouse in Gloucester

Charming Guesthouse with Access to Private Beach

LeahRating, 5 stars1 day ago

Absolutely beautiful spot and hosts were wonderful. Access to the local beach was an awesome bonus to this adorable spot.

4.95 out of 5 average rating, 42 reviews

Home in Gloucester

Townhouse #1 in Downtown with Parking

TatumRating, 5 stars2 days ago

Cute little house in the perfect area for walking everywhere downtown. Very clean and perfect for 6!

4.95 out of 5 average rating, 55 reviews

A serene harbor scene is depicted at sunset, showcasing vibrant hues of orange and purple reflected on the water. Silhouetted against the skyline, a dog is seen near a cylindrical stone structure on the pier, while boats are anchored in the gentle waves.

Home in Rockport

Charming waterfront home. Patio, Shops & Dining

LyndaRating, 5 stars2 weeks ago

I can’t thank you enough for letting me stay in this beautiful location. I’ve been going through chemo treatment and trying to find beautiful places in between treatment to enjoy. This place was a fav. Which I sort of want to keep to myself. I didn’t have a lot of energy to do a lot but it was exactly what I needed. Parked my car and left it behind. Watched the tide, walked around a beautiful place with my dog. I couldn’t ask for more.

4.96 out of 5 average rating, 53 reviews

CbytheSea - Ocean View Penthouse

InvaRating, 5 stars3 days ago

Spent Father’s Day weekend in Gloucester with immediate and extended family, and rented both units from Nick and Emily. I must say the whole family absolutely loved everything in the units. I feel like pictures don’t do it justice as it felt way bigger in person. So well decorated. Super clean. Amazing location!! Finding parking wasn’t teeeerrible, just slightly inconvenient. There was always plenty if you were willing to take a short walk. Nick and Emily were super responsive and extremely accommodating. Hoping we can all return once this New England weather warms up enough to enjoy the beaches.

Superhost

4.88 out of 5 average rating, 81 reviews

Annisquam Village Abode - access to private beach

JohnRating, 5 stars7 months ago

overall, this was a wonderful stay. Susan is extremely friendly, honest, and a very gracious host. She had a bowl of fresh fruit waiting for us along with Milk, Orange juice, English muffins, butter, and cereal; things I was not expecting and have never had before at an Airbnb. The unit was immaculate and exactly as the pictures showed. I asked for recommendations on a few things to do and she provided links to yelp pages almost immediately. I believe Susan lives in a different part of the house, but we still felt like we had so much privacy. The unit is in a gorgeous little private wooded development not far from the water, and we enjoyed a few walks around the neighborhood admiring some of the beautiful houses and the water view. We had no issue getting an uber to and from Glaucester to attend the wedding we were in town for, despite the area being so private. I would absolutely stay here again if we ever find ourselves back in the area!

Superhost

A welcoming front porch pathway is lined with white exterior paneling and flanked by trees, leading to a view of Little River. The house number '30' is displayed prominently, while a patterned mat lies in front of the entryway.

Home in Gloucester

5 out of 5 average rating, 4 reviews

Stay at Little River

DavidRating, 5 stars1 month ago

Great place to stay- extremely relaxing and beautiful surroundings. The view was amazing to wake up to every day. The house was very clean and had everything you would need. Allie was a great host. I would 100% recommend and stay here again myself.

Guest suite in Gloucester

A scenic view of a beach at low tide, where the water's edge reveals wet sand glistening under sunlight. Waves gently lap at the shore, and a distant building is visible against the backdrop of a cloudy sky that suggests an evolving landscape.

4.9 out of 5 average rating, 79 reviews

Charming, Friendly, Quiet, Hilltop Neighborhood

NadirRating, 5 stars3 weeks ago

Excellent place to stay with small family of 3-4 conveniently located to the Gloucester Harbor and main street and some fabulous restaurants, enjoyed my stay nice hikes, whale watching trip and awesome food experience.

A cozy outdoor seating area is present, featuring a loveseat adorned with a colorful cushion and a wooden coffee table. Lush greenery surrounds the space, with stepping stones leading to the entrance. A fence in the background offers privacy while natural elements enhance the tranquil setting.