Vacation rentals with outdoor seating in Gloucester

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!

Tiny house experience steps from the water!

-Tiny house experience in quiet private neighborhood on its own lot with great backyard & fire pit on private secluded St. -prof cleaned after each guest -High speed internet/ expanded cable -Built in full bed with queen sleeper futon bed that can sleep 2 more -Just a few steps from beautiful Dudley Pond for swimming/fishing and great walking trails Wayland is one of nicest towns in MA yet only a min or two from anything you need and less than half hour from Boston. texts returned instantly

Gorgeous Retreat - Amazing Kitchen - Hosts 6

PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino Whether you travel for outdoor adventure, beach time, family bonding or just hanging out, this gorgeous two-bedroom home – just minutes away from the beach and Encore Casino and less than 20 minutes from the city center – was lovingly renovated and outfitted to curate an experience of being at home, at peace, and surrounded with quiet beauty. Restaurants, Grocery Store, Pharmacy and other conveniences within minutes walk.

Get to The Point, Winthrop

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy one bedroom, private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets

Waterfront Paradise! Sweeping ocean river 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).

A water view slice of heaven at Pepperrell Cove

Enjoy the peace and tranquility of staying in Kittery Point Maine’s exclusive Pepperrell Cove area. • Walk three minutes to dinner at one of three amazing waterfront restaurants • Enjoy a private chartered boat ride from across the street • Rent kayaks • Visit Fort McClary • Hike Cutts Island Trail • Visit Crescent and Seapoint beaches • Shop and dine in Kittery’s Wallingford Square, downtown Portsmouth, and the Kittery Outlets. Everything is within fifteen minutes away!

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!

View of Marsh & Dunes| Pet Friendly| Wkly Discount

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!

Historic home w/ charming courtyard

Charming downtown home, newly renovated, near waterfront, private garden. 5 miles to downtown restaurants and shops. Quiet neighborhood. Peaceful patio. Not for large groups. Quiet must be observed in outdoor spaces. Be respectful of neighboring homes and keep outdoor conversation to an intimate, quiet level. Free parking lot on corner with park setting and playground.