There are few "chain" hotels on the North Fork. These maintain the degree of hospitality, cost, and ambience for which the corporations are known. Far more motels/hotels/inns are privately owned. Those listed below have been personally visited by North Fork Weddings.
Cliffside Resort Condominiums on the Sound at Greenport
61475 Route 48
Greenport, NY 11944
(800) 269-4140 or (631) 477-1818

This brand new condo resort is stupendously located on the North Fork of L.I, and is one of only a handful of places with water views. The sunset views are not be outdone anywhere in the world. Not only is the resort new, but this concept is rare on the East End which has mostly small motels/hotels and B&B's. Short of owning your own place or renting a house for the season, this is a very comfortable, convenient, and luxurious way to spend time out east. All condos are two bedroom/ two bath, sleep 6, have flat screen tv's, full kitchenettes (even a wine chiller!) and wi-fi. There's a heated swimming pool and laundry facilities on site and if you have a large group or family, it offers multi unit special pricing. It is located only minutes from the Village of Greenport and the Shelter Island Ferry providing traffic free access to the Hamptons. I found the pricing surprisingly affordable so if you plan a visit this summer, you may be one of the resort's first guests!
Dreamer's Cove Inn
15 Bay Avenue
Aquebogue, NY 11931
(631) 722-3212

If your idea of a fun weekend on the North Fork is to sip some Long Island wine while sitting in your comfortable room overlooking Peconic Bay, Dreamer's Cove Inn may be the answer.  Every single room is waterview!  Kayaks are available for use right on the inn's private beach and a wide sprawling lawn is ideal for BBQ's, weddings (it can hold a huge tent), frisbee, or just searching for four leaf clovers.  A casual beachy atmosphere prevails with all rooms having beautiful light oak floors, wide windows to allow for sublime viewing, and even kitchens/kitchenettes.  This is the perfect spot for groups to get away as the sixteen rooms all not only look out on the water, but are all on the same level.  Imagine the fun the kids, your fraternity/sorority friends, or your wedding guests can have here.  The inn is under new ownership and management and the manager Chris was raised out east.  (He's also an veteran of Iraq.)  The rooms are large and some are especially romantic.  Do remember that this is a beach side inn and has that a seaside feel, not a Victorian B&B feel.  It is very conveniently located near all the wineries and is only about 15 minutes from the last exit off LIE.  If you want to hold a party, Chris will be glad to help you make it a really fabulous event.  (See Venues)
Harborfront Inn at Greenport
209 Front Street
Greenport, NY 11944
(631) 477-0707

The Harborfront Inn is a 21st century luxury hotel smack dab in the middle of a Norman Rockwell scene. The counterpoint of modern design in the lobby with its dark wooden floors and unique architectural details against the delightfully small town ambience complete with a carousel in the park and ships in the harbor balances perfectly. All rooms are spacious and have such amenities as Frette™ linens, flat screen televisions, CD stereo systems, high-speed internet access and massaging body sprays in the showers. (The bathrooms are just amazing, especially the Terrace Suite with its Jacuzzi tub!) The suites are truly magnificent, the largest having its own private 900-square-foot deck overlooking Mitchell Park, Greenport Harbor and Shelter Island. I just can't imagine a more romantic spot for a bride and groom. Many of the 35 rooms have similar views that are gorgeous by day or night. Every attention to your comfort and pleasure has been given: complimentary continental breakfast in the lobby in front of a fireplace and curved bar, local art in the hallways, lobby and guest rooms, a fitness center and inviting furniture. The hotel has been featured in many national publications and has received accolades from everywhere. It is convenient to all wineries, restaurants, shops, ferries, trains and buses. Truly a luxury, it is one you can't afford to miss.
Heron Suites
61600 Main Road
Southold, NY 11971
(631) 765-5121

Part of the landmark Port of Egypt Marina, Heron Suites is ideally located dockside at Southold Bay. It sits on the idyllic North Fork, on the East End of Long Island, near pristine bay beaches, farms, vineyards, nature preserves, golf courses, historic Greenport, and ferries to Shelter Island and Connecticut. The 17 well-appointed suites, accommodating two to seven people in studio and two-bedroom units, are fully modernized with the comforts of home including full kitchen and entertainment facilities. Lodging is available year-round and popular with those who boat, bike or hike; attend a wedding, seek a romantic getaway or are in search of a family vacation in nature's finest surroundings.
The Portly Grape Inn and Restaurant
305 North Road
Greenport, NY
(631) 477-4500

The Portly Grape Inn and Restaurant is what visitors to the East End have been waiting for. Opulent and stately, yet comfortable and cozy, The Portly Grape is both an elegant destination and a comfortable retreat. Each room is individually decorated, complete with a king sized bed, grand furnishings, a fireplace, and most have balconies. For a large group of family and friends looking for an extended stay The Portly Grape offers 2 and 3 bedroom suites complete with living room, dining area and outdoor patio overlooking secluded grounds and a neighboring vineyard. What could be better for a destination celebration? Continental breakfast is included with your overnight stay.
The Pridwin Hotel
Shelter Island, NY
(631) 749-0476 or (800) 273-2497

There are very few resorts on the East End of Long Island and nowhere is there one more beautiful than The Pridwin Hotel. Located on the famous Crescent Beach on Shelter Island, this property offers guests a wide range of experiences. You can read by the pool, play a game of tennis, swim in the clear salt water, bicycle the shady twisty roads, golf, hike, kayak or kick back! The hotel is available for weddings, corporate events, and family vacations. Rooms are booked quickly in season, so be sure to make reservations early. My favorite time on Shelter Island is early fall, so be sure to ask about rates for this time of year also.
The Sound View Inn
58775 North Road (Route 48)
Greenport, NY 11944
(631) 477-1910

If you love the beach, this is the place for you! Each room overlooks the Long Island Sound and has its own private deck and beach! The rooms are decorated simply but nicely and there are suites available. Children are welcome though there are some suites that are for adults only. It has a swimming pool, tennis courts, and cocktail lounge. One of my friends always has her parents stay there as her mother is wheelchair bound and the inn is so easy to navigate for the handicapped. Parking is directly outside the rooms and there are few, if any, steps through the entire establishment. The Soundview Inn is the only real resort facility on the North Fork.