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Vacation rentals in Essex

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Top-rated vacation rentals in Essex

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Guesthouse in Annisquam
4.97 out of 5 average rating, 288 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
Cottage in Essex
4.96 out of 5 average rating, 114 reviews

Lakefront cottage for a fun, relaxing getaway.

Enjoy a cozy stay in a lake front cottage. Located in Essex, on chebacco lake, this 3 bedroom, 1.5 bathroom home has everything you could need. Fully stocked kitchen, comfortable living space with wifi and a large TV, and a comfy couch overlooking the lake. We have a external monitor with a keyboard and mouse to set up a workstation if needed. A large deck and seasonal dock to hang out on. Close to the ocean if you get tired of the lake. It's an excellent home base on Boston's North Shore.

Top guest favorite
Apartment in Rockport
4.98 out of 5 average rating, 221 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.

Top guest favorite
Apartment in Rockport
4.99 out of 5 average rating, 140 reviews

4 Bed 2.5 Bath Water view Downtown with Parking

Your family and friends will be close to everything when you stay at this centrally-located home. Steps to the Ocean and walk into historic Bearskin Neck. Enjoy panoramic coastal views from the family room, kitchen and master bedroom. Deck space to enjoy outdoor dining, glass of wine, or a morning cup of coffee. Everything to do in Rockport is a short walk from this downtown home. Restaurants and coffee shops, Art Galleries, shopping and the town beaches are steps away. Parking spots included.

Top guest favorite
Apartment in Ipswich
4.99 out of 5 average rating, 176 reviews

Charming 2 Bedroom Apartment in Historic Ipswich.

In the heart of historic downtown Ipswich, the John Brewer house has been a family home since 1680! This fully renovated apartment features many modern amenities, like hi-speed internet, 50" and 55" televisions with streaming channels. There is parking for two cars, and we are a short walk to Market Street, the commuter rail to Boston, a large park for children, and many fantastic local restaurants. Drive to Boston or Maine in 45 mins; Salem or Gloucester in 30 mins; Crane Beach in 10 mins!

Top guest favorite
Condo in Essex
5 out of 5 average rating, 44 reviews

Marshside one-bedroom with stunning view

Convenient and sparkling clean, this fully furnished apartment is minutes from everything Cape Ann has to offer, but you might choose to stay put and enjoy the scenery instead! Enjoy the stunning marsh view with deer, hawks, osprey, and more, or head out to enjoy Cape Ann's other treasures. Located just off Rt. 133 in Essex, we're a short walk from the Essex County Greenbelt headquarters, a slightly longer walk from Conomo Point, and an easy drive to clam shacks, antiques, beaches, and more.

Guest favorite
Apartment in Magnolia
4.86 out of 5 average rating, 120 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.

Guest favorite
Guesthouse in Hamilton
4.88 out of 5 average rating, 226 reviews

Lake View New England Cottage in Hamilton, MA

The Cottage is in rural Hamilton on the North Shore, just 40 mins from Boston. The property is set in grounds beside Lake Chebacco, with lovely waterfront views of the lake. The Cottage is a tranquil retreat, just a few minutes drive away from Cranes Beach, Ipswich, Cape Ann and many beaches and walking trails. Both Gordon College and Gordon Conwell are under 10 minutes drive away. Popular Salem is just 20 minutes drive away. Off street parking for 1 car. No children <15 due to safety

Guest favorite
Apartment in Ipswich
4.99 out of 5 average rating, 142 reviews

Unit 2~Garden Getaway Close to Beach & Downtown

Holly House 2 is our 2nd floor Victorian vacation rental within close proximity to downtown, beaches, train, hiking, kayaking, biking, restaurants & shopping! Enjoy a stylish experience in this lovely home away from home with dedicated work space, comfy bedrooms/living room, in unit laundry & well stocked kitchen. A great retreat for couples, families, remote working/learning, nature enthusiasts, beach lovers, corporate stays, girl's weekends, holidays stays & more!

Top guest favorite
Cottage in Essex
4.95 out of 5 average rating, 285 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
Home in Ipswich
4.97 out of 5 average rating, 116 reviews

Hillside

Perfectly situated within steps of Pavilion Beach and Pirate Park Playground. Makes for a great family getaway! Highchair and pack & play available! Wake up to this sun-filled home with water views from almost every window in the house! Enjoy the wraparound deck with lots of space for outdoor entertaining while taking in the spectacular views! The kitchen is well equipped with all new appliances, including a Viking range for those who love to cook.

Top guest favorite
Cabin in Rockport
4.97 out of 5 average rating, 468 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.

Popular amenities for Essex vacation rentals

Quick stats about vacation rentals in Essex

  • Total rentals

    40 properties

  • Nightly prices starting at

    R1,736 ZAR before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Essex?

    Essex has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Essex have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Essex. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Essex have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Essex. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Essex?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with a kitchen, over 20 homes with free parking, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Essex?

    Yes! Work meets play with ease at over 20 vacation rentals in Essex featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Essex?

    Four-legged friends are welcome in Essex. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Do house rentals in Essex have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Essex. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Essex have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Essex. Enjoy a tailored experience with all the comforts you desire.

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