Holiday rentals with outdoor seating in Essex County

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Top-rated rentals with outdoor seating in Essex County

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Guest favourite

Place to stay

4.94 out of 5 average rating, 16 reviews

Historic District

Beautiful historic house fully remodeled in the center of the historic district. Cafes, shopping, restaurants, beaches, harbor all in minutes of walking distance. The second bedroom is on the 2nd floor and is it's own small unit with a king size bed, sitting area, half bathroom, refrigerator, and coffeemaker. the main area has a lovely living room, office, sit in kitchen, bedroom with a queen size bed and a fullbath. Outside sitting area with a BBQ grill, fire pit, lounge chairs. Onsite parking

Guest favourite

Cottage

4.84 out of 5 average rating, 111 reviews

Designer decorated-Sunset Bliss- Beach 3 min walk

Peaceful Plum Island cottage, renovated fall of 2018 and 2023 with New England coastal charm. Open floor plan and water views of the marsh, a short 3 minute walk to the beach. Watch the sun rise over the Atlantic and enjoy the spectacular sunset directly in front of the house for a nightly show. Walk the cottage for ice cream, Rip tide & the Sunset Club for cocktails and dinner. Beach, boating, fishing, wildlife sanctuary, and the historic downtown Newburyport all just 40 miles from Boston!

Guest favourite

Home

5 out of 5 average rating, 31 reviews

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!

Guest favourite

Flat

4.89 out of 5 average rating, 103 reviews

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

Guest favourite

Flat

4.88 out of 5 average rating, 126 reviews

View of Marsh & Dunes| Pet Friendly| Wkly Discount

***WINTER RENTAL AVAILABLE*** Inquire about winter rental rates for stays 2 months + Welcome to this truly unique property situated on one of the largest lots in all of PIum Island making it the perfect spot for outdoor entertaining! Enjoy the seclusion of this spectacular, scenic lot while being conveniently located just a short half block walk from the Sunset Club, Plum Island Grill, Beachcomba and The Cottage Creamery and also just a 7 minute walk to the beautiful Plum Island Beach!

Guest favourite

Bungalow

5 out of 5 average rating, 108 reviews

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!

Guest favourite

Home

5 out of 5 average rating, 14 reviews

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.

Guest favourite

Home

5 out of 5 average rating, 9 reviews

Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets

Waterfront Paradise! Sweeping ocean views & gorgeous sunsets! Swim, paddle board or watch the tides come and go on the private dock and raft. Enjoy a book, nap or meal on the screened-in porch or patio. Bring your own boat and cruise the day away. Close to beaches - Stage Fort (5 min) and Good Harbor (12 min) as well as cafes, shops and nightlife in town center (10 min).

Guest favourite

Flat

4.98 out of 5 average rating, 126 reviews

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.

Guest favourite

Flat

4.95 out of 5 average rating, 172 reviews

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

Guest favourite

Home

4.94 out of 5 average rating, 152 reviews

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!

Guest favourite

Apartment

4.96 out of 5 average rating, 100 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!