Hotels in Dering Harbor

Stylish rooms in this boutique hotel offer a peaceful retreat after exploring the harbor. Unwind with a drink at the bar, grab a bite at the coffee shop, or bike to nearby Greenport Harbor Brewing Company and Farmers' Market.

Perched oceanfront in Greenport, this hotel offers a seasonal outdoor pool with poolside bar. Just a short drive from the Railroad Museum and The Old Field Vineyards, enjoy American cuisine at The Halyard restaurant and unwind at 2 welcoming bars.

Overlooking Greenport Harbor, this boutique inn combines coastal charm with modern comforts. Just a 3-minute walk from the train station, guests enjoy the seasonal outdoor pool, 24-hour fitness center, and complimentary breakfast while exploring nearby attractions.

Wake to island tranquility at this Shelter Island Heights hotel with premium bedding. Near Shelter Island Country Club and Sunset Beach, this refined retreat offers free WiFi and parking. Convenient to Greenport Station for day trips.

Tucked away in Shelter Island Heights, this golf-adjacent hotel offers a seasonal outdoor pool and rejuvenating massage services. Enjoy cocktails at the poolside bar, grab bites at the restaurant or deli, then explore nearby Sunset Beach and Shelter Island Country Club.

Dive into waterside charm at this Southold retreat on the bay. Located near The Old Field Vineyards and Crescent Beach, the hotel offers free WiFi, bicycles, and a cafe/bar lounge. Travelers consistently praise the helpful staff for enhancing their stay experience.

Perched on the bay, this coastal retreat offers a private beach, outdoor pool, and spa with hydrotherapy treatments. The seasonal restaurant serves local cuisine while proximity to Crescent Beach and Sunset Beach enhances your island getaway.

Explore Greenport from this stylish inn with its welcoming bar and restaurant. Grab the complimentary bikes to visit nearby Greenport Harbor Brewing Company. The attentive staff and daily housekeeping ensure a carefree stay, just an 8-minute walk from the train station.

Escape to this stylish Greenport retreat offering free breakfast and WiFi. Relax at the rooftop terrace or grab a drink from the bar before exploring local attractions on complimentary bikes. Only a 3-minute walk from Greenport Station, near Camera Obscura.

Wake up to a fresh continental breakfast at this coastal B&B offering a seasonal outdoor pool and complimentary bicycles for island exploration. Located near Shelter Island Country Club and Sunset Beach, guests enjoy free WiFi and parking in this tranquil garden setting.

Tucked beside Old Saybrook Station, this peaceful inn offers comfortable beds and free parking. Explore nearby Chalker Beach or hike local trails before relaxing in clean rooms. Himalaya Café and The Teakettle Cafe are just steps away for tasty meals.

Wake up to seaside charm at this Clinton motel where the ocean beckons nearby. Take a refreshing dip in the seasonal outdoor pool after exploring Clinton Plaza or the historic Adam Stanton House. Free WiFi and parking add value, with Clinton Station just a 19-minute walk away.

Relax at this peaceful hotel with an indoor pool and fitness center. Just a short drive from Old Saybrook Station, enjoy American cuisine at The Comfort Cafe and unwind at the bar. Free breakfast, WiFi, and parking add value near popular local attractions.

Experience peaceful slumber in this quiet hotel near Essex Saybrook Antique Village. Minutes from Ferry Landing State Park, the hotel provides free WiFi and parking. Nearby kayaking adventures and attentive staff create a refreshing coastal getaway.

Wake up to complimentary breakfast at this waterfront hotel, just moments from Sag Harbor Whaling Museum. The outdoor pool offers refreshing relaxation after exploring nearby attractions. Free WiFi and parking enhance the value, while the attentive staff ensures a memorable stay.

Tranquil accommodations near Tanger Outlets and Crystal Lake Town Park offer a quiet escape. Take advantage of free weekend breakfast, WiFi, and parking. Only a 4-minute drive from Old Saybrook Station for convenient regional travel.