Hotels in Oak Bluffs

July 17-24 Cape Escape Oceanview 1-bdrm sleeps 4

Cape Cod escape at InnSeason Resorts Captain’s Quarters Surfside in beautiful Falmouth, MA! This bright 1-bedroom timeshare sleeps up to 4 perfect for couples, families, or small groups looking to enjoy a classic Cape Cod summer. Easy walk to Falmouth Heights Beach and just minutes from dining shops, and ferry to Martha’s Vineyard ✦ Close proximity to Falmouth’s beaches ✦ Outdoor pool & lounging spaces ✦ Scenic views of Vineyard Sound ✦ Washer & dryer access available (check resort amenities)

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.

Custom padded headboards & thoughtful perks

We offer a cheerful and cozy first-floor Queen room at The Christopher, complete with a plush queen bed, charming architectural details, and an occasional chair. This well-appointed room features a 32" flat-screen TV, in-room safe, a compact private bath with shower, individually controlled AC and heat, and free high-speed WiFi. Please note, this room is near the front door and front desk, so some foot traffic noise may be experienced. For any questions, feel free to call the hotel directly.

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.

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.

Cozy, petite room on the second floor

The coziest rooms at our new Martha's Vineyard boutique hotel, The Edgartown Inn's two (2) queen rooms are located on the 2nd floor and can accommodate two guests each. These rooms offer all of the amenities of our others, at just a more petite size. You'll find a plush queen bed, LED Smart TV, mini-fridge, safe, blackout shades, and USB outlets, in addition to individually-controlled AC and heat, and free wireless internet.

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 reno’d, 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.

Studio apartment across street from Ocean beach.

JUST REDUCED. Beachside is on the ocean. This is my time share that I cannot use this year. The dates are Oct. 10 to Oct. 17. THIS is a great location, just a few minute drive to Woods Hole, and the ferry to Martha's Vineyard. It is a studio apartment with all the amenities. MINIMUM 2 NIGHTS. / NIGHT

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.