Hotels in Oak Bluffs

Outdoor fire pit with modern wicker seating

The three (3) King Deluxe rooms at our boutique Edgartown hotel can accommodate two total guests each. Varying from 245-280 square feet each, one is located on the second floor adjacent to The Richard and King Suites (great for groups traveling together). Each room offers a plush king bed, and each its own unique style and function. All of these rooms also offer a 43" LED Smart TV, a safe, blackout shades, and USB outlets, in addition to individually-controlled AC and free wireless internet.

Sip drinks under fringed umbrellas at Pelican Club

Kelley House offers a charming blend of history and modern comfort in the heart of the property. Each room is thoughtfully designed with contemporary amenities, including luxurious Byredo Gypsy Water bath products, a stocked minibar, and a nostalgic Victrola Bluetooth record player. You'll enjoy a serene retreat within walking distance of the property’s key attractions. Perfect for couples, families, or solo travelers seeking an authentic, cozy experience.

Breezy coastal haven by the Vineyard’s farms

Our Edgartown boutique hotel offers five (5) King Deluxe rooms, each able to accommodate two total guests each. Located on our 1st and 2nd floors, with 200-230 square feet each, these rooms offer a little more elbow room then our King rooms as well as a cozy sitting chair. Each room offers a plush king bed, LED Smart TV, mini-fridge, safe, blackout shades, and USB outlets, in addition to individually-controlled AC, and heat and free wireless internet.

Maritime vibe with knotty pine & iron-frame beds

The Coonamessett offers two (2) comfortable 1st-floor King junior suites that are both ADA accessible. One large space features a plush king bed and a lounge/sitting area with a sofa and dining table as well as a private bath with a walk-in shower. These 475-510 square foot rooms also include a 43" Smart TV, Bluetooth radio, mini-fridge, individually-controlled AC and heat (window AC units used in the warmer months), and free wireless internet access.

Ideal spot near Main & Water streets

Our Queen rooms are bright and inviting, featuring a plush queen bed and practical storage with either an armoire and small bench or a closet and dresser. Each thoughtfully designed room includes an occasional chair, a 32" flat-screen TV, in-room safe, charming architectural details, and a compact private bath with shower. Enjoy individually controlled AC and heat, plus complimentary WiFi for a comfortable and connected stay.

Near Falmouth Beaches + Pool. Dining. Bar.

Escape to Cape Cod at Iris Hotel Cape Cod—just minutes from beaches, bike trails, and ferries to Martha’s Vineyard. Unwind in the indoor pool, hit the gym, or grab dinner at the on-site restaurant. You’re close to downtown shops, waterfront walks, and the Shining Sea Bikeway. With free Wi-Fi, parking, and all the essentials, this laid-back coastal stay is perfect for beach days, lobster rolls, and easy Cape vibes.

Partial Ocean View Studio| Kitchenette & Deck(105)

Stay just steps from the beach in this bright studio featuring two double beds, a convenient kitchenette, and shared deck access with partial ocean views. Perfect for couples, friends, or small families, this room combines comfort with a prime oceanfront location. Relax after a day in the sun, explore nearby shops and attractions, or enjoy fresh coastal dining at the on-site oceanfront restaurant.

Fully renovated, overlooking the blue harbor

Our intimately sized Queen rooms feature a plush queen bed, private bath with compact shower, 43" LED Smart TV, and Tivoli bluetooth radio. Other features of this very affordable room include individually controlled AC and heat and free wireless Internet access. Please note: rollaway beds may be available at an additional cost, please contact the hotel directly to inquire about reserving one.

Unique décor & furnishings in every room

Room 3 is an intimate king room located in a cozy corner on the 2nd floor of The Coco. This 125 square foot space offers high ceilings, hardwood floors, 40" flat screen TV, plush bathrobes, Lather bath products, and a private bathroom with a shower. Other elements include Japanese-inspired coastal wallpaper, a scalloped bed frame, fringe chandelier, walnut armoire, and a comfy reading chair.

Innseason Captain's Quarters | 1 Bed | July 3 - 10

The Captain's Quarter's has been rated by RCI as the best resort at the Cape! Located on the 2nd floor - One bedroom, two full bathrooms. Full Kitchen and large balcony overlooking Falmouth Heights Beach which is less than 100 feet away! Sleeps 4 comfortably with over 700 square feet. In walking distance to everything, including some of the most popular restaurants and bars!

Inn on the Square - Two Queen Guest Room

This beautifully furnished guest room features two queen size beds. Amenities include new luxurious bedding package with high thread count linens, feather bed with duvet and premium pillows. Bathrooms have hairdryers, granite vanity and distinctive bath amenities.

Don’t miss the daily small plates breakfast

The KD room at Hotel The Sydney offers a plush king-size bed in a stylish, contemporary setting. Enjoy modern amenities, elegant decor, and a comfortable retreat that’s perfect for unwinding after a day exploring Cape Cod.