Holiday rentals in Old Field

Cottage in the heart of Stony Brook Village

Stay in a fully renovated 100-year-old cottage that blends historic charm with modern comfort. This is the perfect cottage for couples, families, or small groups. Walk just ¼ mile to Stony Brook Village shops, restaurants, the fishing pier & beach, or watch the wildlife from your screened-in porch. Only an 8-minute drive to Stony Brook University & Hospital. Experience the perfect mix of village charm, modern amenities, and natural beauty. 2 Queen private bedrooms + full size sofa bed. Sleeps 5

Newly done basement apartment Great location

Keep it simple at this peaceful and centrally-located place. A spacious private apartment located at our family home - has a separate entrance and driveway parking.. It is conveniently located off major roadway, which offer a quick access to the LIE, just a 5 minute ride to the Port Jefferson -Bridgeport ferry, and the scenic Port Jefferson Village and the LIRRalso Mather and St. Charles Hospitals 10 minutes to Stony Brook Hospital and University. Close to many restaurants and local beaches.

The Historic 1813 House

Recently restored, this Port Jefferson Village historic house has all of the amenities of today. Boasting 3 bedrooms and 2 full bathrooms, a short walk to the busy day and night life of Main Street. Watch the sunrise from the top bedroom over the port and watch ferry boats as they arrive throughout the day. Read a book in the beautiful all wood sitting room or take a bath in the recently restored cast iron claw foot tub. This house offers quiet serenity with an option to explore the village.

RP modern cozy cabin

Have fun with the whole family at this NEW all electric smart home. It's just a few minutes to the Long Island Sound, 15 minutes to Baiting Hollow Farm Vineyard and a 5000+ acre preserve just to the south. In addition we have so many local amenities including the prestigious "Fish Church of Rocky Point", food spots, Starbucks & more. The sound is known for beautiful sunsets, sun tanning, paddle boarding, bike riding and fishing. The pebble beach is great to walk on with shoes or bare feet.

The Buccaneer Suite ~ Your Private Seaside Escape

Come be enchanted with The Buccaneer, a private, luxurious yet charming two-bedroom duplex suite nestled within Falaena House Inn - our historic, eco-conscious retreat. Blending coastal elegance with maritime spirit, The Buccaneer offers a rare sense of seclusion while placing you a mere two-minute stroll to the beach, local shops & coastal eateries. At Falaena House Inn, we care deeply for the land, the sea, and you! We welcome you home like a captain to port (adult-only, no-pets).

Port Jefferson Convenient, Cozy and Chic!

Bright, modern, newly renovated and landscaped space can sleep up to 6! Countless amenities including a kitchen with dishwasher, full size refrigerator. 3 bedrooms, 2 full baths, and common living space. Great for boaters or attending events in Port Jefferson, Stony Brook or anywhere on Long Island. We are a 1 minute drive or 10 minute walk from Port Jefferson Harbor and Ferry Dock. Centrally located on LI for easy access to LI rail road and bus routes.

Cozy Coastal Escape

Brand new apt in secluded yet convenient location. Nestled in historical area, only 3 miles to SUNY Stonybrook, 4 mi to Pt Jefferson. Separate driveway & entrance, 2 Story Open Concept, Full size eat-in Kitchen, Living Room with sleep sofa, Queen Bedroom, Bathroom & separate Work Area. Key lockbox entry, Complimentary coffee/tea, air mattress/extra linens upon request. Close to Stonybrook village, exquisite local waterfront parks, restaurants & shopping

Studio in Stony Brook

We have contactless check-in procedure & fully private entrance. Please contact with any questions! Large clean studio space that is totally private from the main residence. Private bathroom with toiletries included. Close to beaches, shopping, and SUNY hospital and campus by car or bus. Pull-out loveseat with twin size mattress available for an extra charge. (Book for “3 Guests” for this regardless of occupancy so we know to prepare the bed.)

Luxury modern farmhouse with heated pool & hot tub

*Pool is now open until late October This beautiful modern farmhouse is located on a one-acre lot and features a custom designed open-concept living space with vaulted ceilings that opens directly into a pool area. Hidden behind a bookshelf, you'll find a gorgeous game room with a piano and a pool table that can be easily converted into a ping pong table or working space. Please note that we do not allow weddings and events at this time.

The Katalpa House -by the beach

-Our beach is private, key and beach tag provided- (in brown shed) This 1000+ sf home, features a newly renovated kitchen, outdoor shower, and many quirks that come with a 90 year old home. The furnishings are eclectic and vintage. Most of the flooring is also new. The beach and bluffs are only about a 2 minute walk. The 1/4 acre lot is shared with a secondary unit as you can see in the photos which is occupied by my sister.

Ocean House

Rare opportunity to rent your own 100’ Private Beach Front Oasis and enjoy all four seasons! This one-of-a-kind gem on a full sandy acre is only 60 miles from NYC. Brand new chef's kitchen w. Viking appliances. Living room w. wall of glass showcasing the breathtaking views of the Sound. The home also has a hot sauna & in sauna shower. Port Jefferson ferry (5mins away) connects you to New England. Our prices are not negotiable.

Harborfront Star Walk to Harbor & Village

** Airbnb Fees are now included in the nightly Rate* **Coastal Retreat** Perfectly located just steps from the waterfront, placing you within easy walking distance of the marina, Harborfront Park, boutique shops, cafés, restaurants, and the ferry. Whether you’re here for a relaxing getaway, visiting Stony Brook, or exploring Long Island’s North Shore, this home offers the perfect blend of comfort, style, and location.