Holiday rentals with outdoor seating in Gloucester

Anchors Away Inn Cozy Walk to Beach, Courtyard

A minute walk across the street to your private beach. Walk on picturesque Cadish Ave to Marina and Local 02045. Drive 5 mins to Kenberma shops. A 7 minute drive to main beach restaurants and bars. Comfy Beds and Bamboo linens. Outdoor shower, private backyard with Lg fire pit and large courtyard with string lights and seating. New AC, Fast-Wifi, dedicated workspace. Dining table for 4 plus a Coffee Bar and a snack or two. Comfortable shower with a seat. Pack & play crib, high chair and games.

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

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).

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.

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!

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.

* NEW Listing * A True GEM in South End , Boston!!

Experience Boston at its Best in this true gem apartment in the heart of desirable South End! Best Location! Best Neighborhood! Best bars and restaurants! A guests favorite in the neighborhood, you will fall in love of this charming 1 bedroom apartment with cozy and relaxing private patio in the heart of historical and trendy South End in Boston.

The River House Salem North Fields neighborhood

Your family will be close to everything when you stay at this centrally-located place. MBTA 5 min. walk, play ground, tennis court and basketball courts across the street. Public access to rivers high tide for kayaking across the st. Great for families and Friends Salem getaway.. There will be tennis rackets, basketballs for your use.