Holiday rentals with outdoor seating in Essex County

Walk to DNTN/Beach/Beauport, Boat Island, New Home

Welcome to The Captain's Quarters! This charming retreat in Gloucester, Massachusetts, features three cozy bedrooms, each with a queen bed, and two modern baths. Enjoy a fully equipped kitchen, smart TV, new appliances, and a private balcony. Centrally located near St. Peter's Park, The Beauport, Pavilion Beach, and the waterfront. Relax in the outdoor spaces, with private parking and pet-friendly accommodations. Book now at this stylish place for a perfect getaway at The Captain's Quarters!

Historic District

This beautiful historic house has been fully remodeled in the center of the historic district. Cafes, shopping, restaurants, beaches, and harbor are all within walking distance. The second bedroom is on the 3rd floor and is a small unit with a king-size bed, sitting area, full bathroom, refrigerator, and coffeemaker. The main area has a lovely living room, office, sit-in kitchen, bedroom with a queen-sized bed, and a full bath. Outside area with a BBQ grill and lounge chairs. Onsite parking

Peaceful sunset retreat (bottom floor)

Welcome to our home at G&T Sunsets! It doesn’t get much better than a quick 4min walk to the beach, followed by a stroll to some of the most iconic local restaurants, & ending with a breathtaking sunset over the marsh. Then pull up a seat at your fire pit to end with s’mores! The serene views & amazing location is the perfect spot to make memories with family & friends on vacation, or a romantic getaway with your loved one. Newly renovated & furnished, come experience an amazing trip!

The Bungalow-Luxe & Cozy Retreat by the Sea

The Bungalow is a coastal chic dream built for two! A newly updated & thoughtfully designed gem, nestled at the northern-most point of Plum Island, Newburyport, MA (not more than 100 paces from the ever watchful beacon of the famous Plum Island Lighthouse). Whether relaxing at the beach, paddling around the Basin, biking to one of the island stores or restaurants , or simply exploring the pristine Federal Wildlife Refuge, a special experience & adventure awaits you at The Bungalow!

Harbor View Walk to Beach & Town, 6Guests KingBeds

Spectacular Gloucester home on Cape Ann. Walk to Stage Fort Park & local beaches right across the street. Gloucester center is about 1 mile. On the way to town, walk by beaches & the park with waterfront tennis & bocce ball courts, plus a great water view playground and playing fields. Just beyond the park is famous Stacy Boulevard with the Fisherman's Memorial Monument along the waterfront. There are beautiful white sandy beaches (Good Harbor, Wingaersheek, Singing, & Crane's Beach).

Adorable renovated house, steps from Front Beach

This charming home was recently fully renovated. The brand new kitchen features stunning granite countertops and stainless steel appliances. The large living/dining room features a 55" flat-screen TV comfy seatingnd a dining table for 4. There is a king bed in the Master Bedroom, along with a TV, ceiling fan, and air conditioning. The second bedroom has a twin daybed, with a second twin trundle bed underneath. The backyard features a patio with a seating for 4 and a gas grill.

Couples Retreat - Apt in Charming Colonial Home

Newly renovated, open concept apartment in a private home located on a quiet residential street. Single, queen-sized adjustable bed, steam shower, and oversized bubble jet tub make this an ideal retreat for stress free relaxation. Includes off-street parking, full-size washer and dryer, and the use of both front and rear porches with seating in season. This apartment is great for couples or individuals looking to relax and get a break from their busy lives.

Entire 1st floor apt in charming seaside Beverly

Enjoy a stylish experience at this centrally-located place. Easy access to downtown Beverly, Salem, local beaches, and commuter rail to Boston. Apartment features a fully furnished living room, bedroom, and kitchen, along with extra amenities including a/c, 𝖶𝗂𝖥𝗂, cable, front and back porch, and outdoor fireplace and patio. Walking distance to all that downtown Beverly has to offer One train stop or 5 minute drive to downtown Salem

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!