Holiday houses in Annisquam River

4.96 out of 5 average rating, 269 reviews

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, 223 reviews

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

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, 301 reviews

Harbor Retreat | Ocean View | Heart of Downtown

Discover Rockport's Harbor View Apartment! 🌊 This newly renovated 1-bedroom on the second level boasts stunning harbor views from a private deck. Steps from Bearskin Neck, enjoy proximity to unique shops 🛍️, fine dining 🍽️, and beaches 🏖️. Equipped with high-speed WiFi, a 55" Smart TV, and a Murphy couch. Perfect for experiencing Rockport's vibrant atmosphere. Note: Guests must climb stairs and the downtown location can be lively and noisy 🌆. Book your unforgettable seaside escape today! ⚓

4.96 out of 5 average rating, 157 reviews

Condo 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.

4.97 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, 257 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

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.

4.87 out of 5 average rating, 214 reviews

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.

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Other great holiday rentals in Annisquam River

5 out of 5 average rating, 32 reviews

Condo in Essex

Marshside one-bedroom with stunning view

KarenRating, 5 stars3 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, 40 reviews

Blue Magnolia

KimRating, 5 stars1 week 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.

5 out of 5 average rating, 9 reviews

Artist Retreat

ShariRating, 5 stars7 months ago

The Artist’s Retreat was the perfect spot for a couple of nights to myself! It’s spacious and quiet and well-appointed. It’s about a 20 minute walk to Main Street, which is full of quirky and fun stores and coffee shops. I would definitely come back! Elizabeth was proactive and responsive and kindly let me check out late, which I so appreciated.

4.97 out of 5 average rating, 34 reviews

Home in Gloucester

Harbor House with Ocean Views

JustinRating, 5 stars3 weeks ago

Harbor House is a great place, conveniently located near downtown, shops, restaurants, and bars are walkable, nice ocean view from the upstairs living room, its an excellent choice for your visit to Gloucester

Guest suite in Gloucester

4.99 out of 5 average rating, 69 reviews

Sunsets at the Seawall - A Coastal Hideaway

DanielleRating, 5 stars2 days ago

This is a comfortable, private, quiet place. It had everything we needed. Loved watching the goldfinches in the garden from the kitchen window in the morning. Hidden gem on Lanes Cove.

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!