Guesthouse vacation rentals in Long Island

Charming 2BR Cottage, Walk to Town

Beech Tree Cottage is a charming 2-bedroom, 1-bath cottage conveniently located in the peaceful historic district of Sag Harbor, NY. It is a 5-minute walk along the waterfront to Main Street and the center of the village. PLEASE NOTE: We have a 1 MONTH MINIMUM stay for bookings in July and August, and 1 WEEK for June until May 15. Thereafter, we accept requests for short stays subject to availability. Please review our booking and cancellation policy and house rules before making a request.

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!

Lakeview Guesthouse with Sauna

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed and the living room has a futon couch which folds down. It’s perfect for 1-2 adults, can comfortably fit 3 people if one is a child.

Entire Guest House at Fox Pond Farm.

Recently renovated private guest house with access to swimming pool offers sleeping for eleven in four bedrooms. Tastefully decorated with all amenities. Close to Merritt Parkway and train to Manhattan. This is a natural refuge on eleven very private acres. Large private terrace faces westerly for amazing sunsets and offers a "Plein Air" environment for alfresco meals, cocktails and relaxation. An attached vegetable and flower garden with fountain offer a quiet space to relax and reflect.

Get Back to Nature at a Modern Wood Clad Getaway

WINTER IS HERE--Glorious winter birds. Come and enjoy a cozy time in our guest house--whether it is a bright sunny day or a beautiful snowy landscape. You can still Hike on the trails. Stroll along the ocean. Ospreys; hawks; cardinals, blue jays, bluebirds, gold finches and more are here year round. Great places to shop and eat or just relax in our cozy guest house. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Cute Little House in Town

Cute little guesthouse steps from bike path. Walk to Main Street or ride bikes to beach. Perfect for two people, but could also work for three with advance notice. There is a queen bed upstairs, and a couch downstairs, there are two fold out cots available upon request. The deck overlooks the huge backyard. The television has a Roku boxes so you can watch Netflix, Amazon Videos, etc. I have a friendly dog named Barney who is often outside on the property.

Gorgeous Waterfront Getaway

Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Private Guest House

Private 600 square foot guest house on side of owners home. Private entrance. Recently renovated with all new bedding, furnishings, bathroom, appliances and fixtures. Located just 1 mile from center of Morristown. Walking distance to many restaurants, parks and shopping. 1 mile from Morristown Train Station, direct to NYC. Plenty of parking, pet friendly.