Oak Bluffs: Victorian Splendor, Oceanside
Walking these streets should be done slowly with your head tilted towards the sights of this seaside community.

For more than three hundred years, the community of Oak Bluffs has been perfecting its craft, ever aware that its fine-grained sand beaches, historically registered Gingerbread Cottages, vibrant night life and light-hearted, brightly colored personality beckons travellers from all over the world.

There's always a reason to go to Oak Bluffs: dining, one-of-a-kind shopping, movies and a steady calendar of events that occur year 'round. Each and every activity is celebrated with the kind of flair and enthusiasm that draws friends and families to its shores time and again.

Please, browse the Property Descriptions and corresponding Property Numbers. Select an accommodation that you would enjoy the most and go to the ‘Book Me Now’ screen to file your request. We're confident that with so many wonderful choices, you'll already be picking out where you'd like to stay when you next visit Oak Bluffs.

With so many attractions, things to do and places to see, it’s easy to miss something. Make sure you visit the "Don't Miss Out' page of this website - it’s a complete listing of everything and anything happening in Oak Bluffs and across the Island.

Property Number Eighteen Built in 1891, this inn is a charming turn-of-the century Victorian bed and breakfast that retains its original carved oak woodwork and features. Seven large, comfortable, rooms with private baths are decorated with period furniture. The rooms have high ceilings and large airy windows. A complimentary continental breakfast is served daily in the dining room. Located just one-half mile from downtown Oak Bluffs, the property features a large front porch with wicker furniture, a large yard with flower gardens, a Koi pond and private parking.

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Property Number Nineteen Quirky, Victorian and perfectly located, this eleven room guest house sits just across the street from Oak Bluffs Harbor. The property features private rooms with shared baths. Some rooms even have private entrances and small porches/balconies. The guest house faces Oak Bluffs marina and is just around the corner from: nightlife, theaters, restaurants, shopping, and art galleries. Ocean Park and Inkwell Beach are a ten minute walk away! Please keep in mind that when staying at this guest house, breakfast is not included nor are the rooms air-conditioned.

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Property Number Twenty A guest house in the Victorian tradition, built in 1876. Seven recently renovated guestrooms are cozy, bright and cheerful and are furnished with antiques. Specific rooms pair ocean views with private decks; all rooms have modern, private baths. Comfortably appointed spacious porches (open and enclosed) wrap around two sides of the property and provide panoramic views of Nantucket Sound. Town, beach, bicycle path and public transportation are just steps away. Sit down and enjoy the tasty complimentary deluxe continental breakfast, which is served daily.

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Property Number Twenty-One This very pretty twenty-two room Victorian-themed inn is located on Oak Bluffs Harbor and features rooms with queen-size beds – in some cases, two queen beds – private baths, televisions, climate control, and telephones. For larger parties or extended stays, the property also features two apartment-styled accommodations. A continental breakfast is offered to all guests on a daily basis as is the six-person hot tub, also located on the premises. Complimentary beach towels and beach chairs are also on hand, on a first-come/first served basis.

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Property Number Twenty-Two Located one mile from downtown Oak Bluffs and one-half mile from State Beach, this condominium property is an excellent choice for a large corporate retreat, convention, or family vacation. Studio units with two double beds, one-bedroom condominiums and two-bedroom, two story townhouses have fully equipped kitchens, private baths, climate control and heat, cable television, telephones and daily maid service. Tennis courts, a fresh-water outdoor pool, 18-hole PGA rated golf course, barbeque area, playground, coin-operated guest laundry and ample parking round out this property.

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Property Number Twenty-Four NEW OWNERS, 'NEW' PROPERTY! This turn-of-the-century newly renovated waterfront bed and breakfast offers nine, completely redone, bedrooms with private bath, television, and air conditioning; some rooms have waterviews where as others overlook the picturesque town. A continental breakfast is included with your stay. The inn is located across the street from Oak Bluffs beach and is a pleasant five-minute walk to town where you will find restaurants, nightclubs, theaters, shopping, and the country's oldest carousel.

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Property Number Twenty-Five Friendly, quiet, comfortable and decidedly casual, this quaint bed and breakfast is located in a quiet residential neighborhood in the heart of Oak Bluffs. The property consists of a twelve room bed-and-breakfast and a separate, up-scale, six room sister property situated across the street. All rooms feature a private bath, Internet access (charges may apply) and all guests are offered a continental breakfast every morning. At the main inn, some rooms can feature refrigerators, balconies and separate entrances. The sister propery, all rooms feature private baths, climate control, balconies, televisions, telephones and stained-glass windows. There are eighteen rooms in total, which are within a short walk to beaches, restaurants, shops, theaters.

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Property Number Twenty-Six Located at the top of Circuit Avenue, this nine room Inn is a proud example of whimsical Victorian-style architecture. Upon entering the century-old gem, the grand porch and antique decor recall a time long past. Although the atmosphere is reminiscent of bygone days, the present day conveniences assure you of comfortable, relaxing accommodations with private bath; a complimentary breakfast is offered every morning. Just a quick stroll to swimming, fine dining, nightlife, and shopping.

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Property Number Twenty-Seven This small, friendly, thirty-five room hotel is situated in Oak Bluffs among Victorian gingerbread cottages. The uniqueness of this property is multi-layered. Hand painted accents decorate some rooms, personal attention by the staff and all day coffee-tea-cocoa service are combined with three different levels of accommodations, built specifically to appeal to every kind of traveler: family vacations, beach-combers, romantic getaways or the budget oriented. Located a block from the ocean beaches and a five-minute walk from downtown dining and shopping. All rooms have private bath and air conditioning. Complimentary continental breakfast buffet and afternoon cookies are included.

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Property Number Twenty-Eight This charming gingerbread house is located in a quiet residential neighborhood, yet within a short walking distance to the beach, nightlife, shopping, restaurants, and art galleries. There are five guest rooms, some with private bath, others with shared bath – one room even features an outside shower! A full breakfast is included and blueberry pancakes are the owner’s specialty!

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Property Number Twenty-Nine Located in the center of Oak Bluffs, this landmark hotel remains one of the oldest hotels in the area. Relax and enjoy the view of the harbor from the spacious front porch. Located just minutes from fine dining, shopping, two blocks from ferries and island transportation and a five-minute walk to the beach. Rooms feature a queen size bed, two double beds or two twin beds; all have private bath, air-conditioning and cable television. Two-room suites and first-floor rooms are also available. This property is comprised of two buildings and has more than ninety guest rooms in total. One note to remember: the main building is a walk-up where as the second building does, indeed, have an elevator.

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Property Number Thirty Wonderfully affordable and superbly located in the heart of the village of Oak Bluffs, this Inn is a charming seaside property just steps away from the beaches, shops and goings-on of Oak Bluffs. Ideal for couples and families alike; fourteen well-appointed guest rooms include private bath, flat screen TV, in-room heat and AC, free wireless Internet service, and complimentary bottled water and snack baskets.

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Property Number Thirty-One Overlooking Oak Bluffs harbor and Nantucket Sound, this motel offers guests a premier location in Oak Bluffs. Close proximity to cafes, shopping, fine restaurants, beaches and historic sites are all at-hand. This is a PET FRIENDLY (additional fees apply) motel that also includes air-conditioning, private phones, cable color television, Broadband internet connection, refrigerators in every room (Jacuzzis and microwaves in select rooms and suites), and plantings. SPECIAL NOTE: certain rooms within this motel have been designated as 'smoking' rooms for those who seeking such accommodations.

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Property Number Thirty-Two This five-room charming country bed and breakfast is just a fifteen-minute walk to a lovely beach. Guest rooms feature either private or semi-private baths. It has a lovely studio for a family with a refrigerator and microwave. In addition to a homemade continental breakfast, amenities include decks, gas grille and an outdoor shower. Small pets are welcome.

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