Boutique hotel vacation rentals in Oak Bluffs

4.91 out of 5 average rating, 11 reviews

A charming wrap-around porch features rocking chairs, a wooden table, and decorative elements like a floral tablecloth and a pineapple centerpiece. Natural light floods the area, highlighting the intricate detailing of the house. The inviting outdoor space overlooks a quiet street and greenery.

Hotel room in Oak Bluffs

Three bedrooms for travel group/excellent location

The Tivoli Inn is a charming Victorian Gingerbread house. The inn is walking distance to all downtown shops and restaurants, in-season ferry terminals, beach, and public transportation. This listing is 3 bedrooms of 6 bedrooms at the Tivoli Inn. These are the family/group travel rooms which share 1 full bathroom, 1 lovely outdoor shower, and an extra sink in 1 of the 3 bedrooms. Bring your flip flops to enjoy the outdoor shower! There are 3 full size beds and one twin bed...a total of 4 beds.

A serene coastal view presents a tranquil blue water scene framed by lush greenery and a pathway. A wooden bench offers a spot to enjoy the landscape, while distant land reveals gentle hills and a clear sky above.

4.85 out of 5 average rating, 47 reviews

Luxury SeaSide King Suite, Frederick William House

The Luxury SeaSide Suite...beautifully appointed, Cal-King suite, pet friendly options with pet fees collected at check-in separately from booking details on Air bnb...located on the Shining Sea Bikeway in Falmouth, across the street from Goodwill Park. Stay includes bike rentals. Enjoy being a short walk to the Steamship Authority parking & shuttle to the ferry boat. Guest are welcome to take bikes over to Martha's Vineyard for day excursions. 139 private and public beaches to choose from.

A decorative fire pit, shaped like a sphere, is surrounded by rocks and illuminated from within, casting a warm glow. The lodge is visible in the background, featuring softly lit windows amid a tree-bordered landscape.

Hotel room in Woods Hole

4.65 out of 5 average rating, 107 reviews

Treehouse Lodge, Canopy style rooms

This beautiful modern meets classic style property is a 10-minute walk from the beach and ferry to Martha's Vineyard in Woods Hole. Free private parking and free WiFi is available on site. Quick walk to the beach, several restaurants, and most science facilities. Guests can enjoy various activities in the area, including windsurfing, fishing and traveling to Martha's Vineyard. *Note to bookers- We are located on the mainland where you get the ferry to go to Martha's Vineyard*

4.77 out of 5 average rating, 79 reviews

A spacious lobby area features a cozy seating arrangement with a light-colored sofa and patterned chairs. A large coffee table is centered on a soft area rug, surrounded by warm wooden beams and greenery. Natural light floods the space through expansive glass doors.

Hotel room in Edgartown

THE FRANKLIN HOTEL~NEW Pet friendly Standard Queen

Located on Upper Main Street in Edgartown, the Franklin Hotel is a short stroll from the heart of the historic village and its famed island beaches. A fresh take on the nautical style with modern, luxury finishes will provide all you need for work, play and relaxation. The Franklin grounds offer distinct seating areas including the covered patio, perfect to enjoy three season island breezes. The chic design of our 18 guestrooms will delight every sense.

The exterior of the bed and breakfast is showcased, featuring a charming gray roof with multiple dormer windows. Lush green landscaping surrounds the entrance, with bright purple flowers and well-maintained bushes in pots. A gravel pathway leads to the welcoming front door.

Hotel room in Tisbury

5 out of 5 average rating, 6 reviews

Luxurious King Room in B&B

Charles & Charles B&B is close to restaurants and dining, the beach. You’ll love this comfortable OAK BLUFFS room with it's luxurious 100% cotton linens, delicious breakfast served pool side and the use of our free bicycles, beach chairs and beach towels. Limited maid service due to Covid 19. My place is good for couples, solo adventurers, and business travelers. All guests must be 12 years or older. For special weekly winter rates, please contact us.

A peaceful coastal view showcases the calm blue waters of the bay, framed by lush green vegetation. A wooden bench sits nearby, inviting visitors to relax and enjoy the scenic landscape, with hints of distant shoreline and trees visible in the background.

4.87 out of 5 average rating, 23 reviews

Harborside G King Suite @ Frederick William House

The Harborside Garden King Suite...beautifully appointed suite, Cal-King pillow-top bed, featuring a grand gas fireplace. Located on the Shining Sea Bikeway in Falmouth, across the street from Goodwill Park. Stay includes bike rentals. Enjoy being a short walk to the Steamship Authority parking & shuttle to the ferry boat. Guest are welcome to take bikes over to Martha's Vineyard for day excursions. 139 private and public beaches to choose from.

4.96 out of 5 average rating, 71 reviews

A charming multi-story building displays intricate architectural details, including decorative trim and multiple balconies. A wrap-around porch is visible, with seating areas for guests to relax. Lush landscaping surrounds the property, creating an inviting atmosphere near the harbor.

Hotel room in Oak Bluffs

In Town Queen Room

The Attleboro House has all of the conveniences of a modern hotel in the quaint atmosphere of a historic inn. Located among the famous Gingerbread Cottages and directly on the Oak Bluffs harbor, you’ll be in the perfect place for your visit to Martha’s Vineyard. Originally built in 1874, The Attleboro House was completely renovated in 2018. Relax on our wrap around porch to enjoy the bustling harbor and impressive views of the Nantucket Sound.

A towering rock formation is silhouetted against a vibrant night sky, where the Milky Way stretches across the frame. Stars twinkle in varying intensities, illuminating the scene while a faint glow hints at distant lights along the horizon.

4.95 out of 5 average rating, 22 reviews

Deluxe Black King Suite @ Frederick William House

The Deluxe Black King Suite...beautifully appointed, Cal-King pillow-top bed, featuring garden and courtyard views is located on the Shining Sea Bikeway in Falmouth, across the street from Goodwill Park. Stay includes bike rentals. Enjoy being a short walk to the Steamship Authority parking & shuttle to the ferry boat. Guest are welcome to take bikes over to Martha's Vineyard for day excursions. 139 private and public beaches to choose from.

4.91 out of 5 average rating, 64 reviews

Glendale Petite @ Frederick William House

The Glendale Petite Room is Double Deluxe Room at Frederick William House. Located on the Shining Sea Bikeway in Falmouth Massachusetts across the street from Goodwill Park. Your stay includes bike rentals. Short walk to the Steamship Authority parking & shuttle to the ferry boat. Guest are welcome to take bikes over to Martha's Vineyard for day excursions. Beach passes are available allowing access all 139 private & public beaches.

4.91 out of 5 average rating, 70 reviews

Park Side Queen Room @ Frederick William House

This beautifully appointed room with private bath & sitting area, includes bike rentals, cable, free WIFI, overlooking gardens & park. We are located on the Shining Sea Bikeway in Falmouth, across the street from Goodwill Park, a short walk to the Steamship Authority. Guest are welcome to take bikes over to Martha's Vineyard for day excursions. Beach passes are available, 139 private & public beaches to choose from.