Holiday houses in Block Island

Private Bedroom/Bath with Separate Patio Entrance

Visit the beautiful west side of BI in your private bedroom apt. with distant ocean and lovely sunset views located on 5 acres of rolling hills. This bright new master bedroom has large light-filled windows, quiet a/c, hardwood floors, en suite bath, and private entrance. Enjoy breakfast on your own patio and dinner cooked on the grill. Walk the nearby greenway trails, to the horse farm for a trail ride, or to the west side beaches for beach combing, fishing, or sunset picnics. Pet friendly!

Ambrose Hideaway

Please come enjoy our charming air-conditioned walk-out basement apartment on beautiful Block Island. The entire space is yours, with a private entrance and private bath. Open your door to an outside patio and enjoy our property on the edge of Ambrose Swamp. Just a ten minute walk from Old Harbor, ferries, restaurants, shops & nightlife. Close enough to hear the ferry's horn, but tucked away from it all next to this scenic marshland. Well-trained, housebroken pets welcome (for a small fee).

Dory Cottage - Blue Dory Inn - Block Island Inns

Escape to our serene coastal retreat! This freestanding cottage behind the Blue Dory is perfectly suited for families or friends, featuring a plush queen bed, queen-sized pull-out sofa, and queen-sized Murphy bed, along with a beautifully updated en-suite bathroom. Savor the efficiency kitchen while soaking in breathtaking ocean views and sounds, and don't forget to bring your furry companion along. “Had a wonderful stay in the Dory cottage. It was clean, bright, and STEPS from the beach.”

Handcrafted Timber Frame Cabin Retreat

Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

New Harbor House Unit A w/Sunset View & Fire Place

Centrally located in the heart of New Harbor, this beautiful home has everything you need to enjoy your time on Block Island. Rent it seperately or combine it with Unit B for an even larger space. This is the ONLY house in the commercial disctrict of New Harbor, yet it is surrounded by conservation land. This means you'll be less than a 10-minute walk to all attractions, but you'll have the peace and quiet of Island life as you take in the sunset over the water from your spacious deck.

Head of Pond House - Waterfront Cottage

Welcome to the charming, waterfront Cottage at Head of Pond House! Enjoy a peaceful retreat with beautiful lake access year-round and pool access from Memorial Day to October. The cottage features two comfortable king beds, including one in a cozy loft area, a full bath, WiFi, a projector for movie nights, and a fully stocked kitchen. Whether you’re looking for a relaxing escape or a comfortable base to explore the Hamptons, our waterfront cottage is the perfect spot for your getaway.

Getaway Suite

We are located high on Mott hill in the center of the island. It's about 2 miles to both harbors. There are lots of hiking trails nearby. We are located near the island airport so small private planes come and go during the day but it is usually very quiet at night. Many of our guests say watching the planes is one of their favorite things. This spot is ideal for visitors who like to retreat to a quieter space at the end of a long day at the beach or an evening on the town.

Charming 3BR Cottage on Pilot Hill

This charming 3 bedroom 1.5 bathroom cottage is everything your family needs for a simple and relaxing Block Island vacation. Located on a dirt road off of pilot hill in a very private location. Large yard with adirondack chairs, outdoor hammock, little dock out to the pond and outdoor seating on the covered porch. Come home after a long day on the beach and wash off in the outdoor shower and then spend the evening watching sunsets on the top deck with seating for two.

Harbor Point Haven

You cannot beat the sweeping views from the patio on this rental on Amy Dodge Lane off of Spring Street. Now rented by Herdman Hospitality, this 2-bedroom (2 queens), 1 full bathroom, and living space is well equipped with modern amenities like a mini fridge, microwave, coffee pot, Roku TV, Wi-Fi, and an outdoor shower. All linens, towels, and beach basics are supplied. About a 5 min drive from the ferry, and less than a mile walk to downtown. Accommodates up to 4.

Vineyard Studio at Spar Point Farm Block Island

Spar Point Farm on Block Island is a 6-acre working family farm including a vineyard, orchard, apiary, gardens, and greenhouse. It offers a winning combination of being well off the main road for privacy and quiet, but less than 10 minutes by car from the main port town and 5 minutes from the airport. The farm is flanked by 230 acres of conservation land to the west and enjoys sweeping views of the Atlantic Ocean, striking sunsets, and wondrous stargazing.

The Ritz: Bright, airy & close to everything!

One of three homes on a large property, the 'Ritz' is a studio with private porch, Adirondack chairs & fire pit outdoors. Perfect for a couple with one queen. A full kitchen, BBQ grill and a short walk to town and the Southeast Light. We may accommodate a child in a pack n play, but do ask you to bring your own linens. The grill is propane, which we provide a tank and a extra. Please let us know if you are out so we can be sure to have it filled in time.

Lower Level of A-Frame | Outdoor Shower + Fire Pit

Stylish lower-level A-frame apartment stay with space for up to 3 adults or a small family. The location is a highlight — just down the road from Rodman’s Hollow, one of Block Island’s most beautiful nature preserves, and close to Cooneymus Beach, a quieter stretch of shoreline perfect for sunset walks. The Lewis-Dickens Farm trail and other nearby paths let you explore rolling meadows, ocean views, and tucked-away coves, all within minutes of the house.