Boutique hotels in Oak Bluffs

A cozy bed is dressed with neutral linens and a striped blanket. A decorative pillow featuring floral motifs adds a touch of charm. A bedside lamp and a white dresser are visible, complemented by a vintage sign reading 'Nantucket Beach Haven' on the wall.

4.87 out of 5 average rating, 53 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.

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The charming Victorian Gingerbread house features intricate architectural details, including decorative trim and a wrap-around porch adorned with flowering plants. Large windows invite natural light, and the sloping roofline adds character to the residence.

4.95 out of 5 average rating, 20 reviews

Three bedrooms for travel group/excellent location

The charming Tivoli Inn is walking distance to all downtown shops and restaurants, beach, in-season ferry terminals, and public transportation. This listing is 3 bedrooms of 6 bedrooms at the Tivoli Inn with common areas with other guests. There is one full bath. In addition there is a 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 to accommodate 3-6 guests.

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A charming Victorian house featuring intricate woodwork and a wrap-around porch adorned with floral elements. Large windows allow natural light to flood the interior. The second floor includes a balcony with decorative railing, enhancing the building's character. Lush greenery surrounds the property.

4.89 out of 5 average rating, 54 reviews

Porch Room 1 queen bed

The Porch Room has a queen bed and private shower room and half bath located next door to the room in the hallway. This bedroom also has its own entrance to the wrap around porch. The Porch room is one of six rooms at the Tivoli Inn. The Tivoli Inn is a charming Victorian Gingerbread house which has the island charm and a clean and friendly atmosphere. The inn is walking distance to all downtown amenities including town beach, seasonal ferry terminals and public transportation.

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4.7 out of 5 average rating, 138 reviews

The room features a spacious bed adorned with a decorative throw, accentuated by a vibrant yellow pillow. Two wooden chairs are positioned next to a side table, with a lamp and a small vase of flowers adding charm. Natural light filters through sheer curtains.

Hotel room in Woods Hole

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*

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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.

4.79 out of 5 average rating, 141 reviews

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.

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A king-sized bed features an ornate, carved headboard and is topped with decorative pillows. A dresser and bedside table are visible alongside a sleek desk with a computer. Soft lighting from two lamps creates a warm ambiance in the space.

4.88 out of 5 average rating, 25 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.

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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.

4.96 out of 5 average rating, 80 reviews

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.

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A cozy room is featured, showcasing a tall, black four-poster bed adorned with decorative pillows and a red floral quilt. A bedside table complements a vintage-style dresser below. A reading corner with a comfortable chair and a bookcase provides a welcoming touch, while sunlight filters through the window.

4.92 out of 5 average rating, 24 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.

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The view captures a well-maintained hotel with white siding, surrounded by lush gardens. A centrally located pool is framed by lounge chairs and umbrellas. The harbor is visible in the background, showcasing numerous boats and a serene sky, contributing to a tranquil atmosphere.

5.0 out of 5 average rating, 3 reviews

Martha’s Vineyard King balcony suite harbor view!

4th floor with large balcony overlooking harbor and pool! Harborside Inn is an excellent choice for rest and rejuvenation. Well-known for its historic environment and proximity to great restaurants and attractions, Free wifi is offered to guests, and rooms at Harborside Inn offer a flat screen TV, a refrigerator, and air conditioning. Very helpful concierge. While staying at Harborside Hotel, you have access to all owners privileges

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A well-lit corner of the room features two white chairs paired with a round table, complemented by a lamp. Natural light streams through two tall windows adorned with sheer curtains. The space showcases a decorative cabinet against the wall and an inviting doorway leading to a private bathroom.

4.93 out of 5 average rating, 81 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.

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A soft, inviting bedroom is highlighted by a spacious bed dressed in white linens. Two decorative lamps with ornate bases sit on either side of the bed, illuminating plush pink pillows against a light-hued headboard. A framed mirror above the bed reflects natural light.

4.93 out of 5 average rating, 84 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.

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The exterior of a Victorian-style house is depicted, showcasing intricate woodwork and a wraparound porch. A flower-filled balcony adorns the front, complemented by well-maintained greenery around the property. The home features multiple gable roofs and a blend of wood siding and shingles.

4.91 out of 5 average rating, 57 reviews

Balcony Room at the Tivoli Inn

The Tivoli Inn is a charming Victorian Gingerbread house which has the island charm and exudes a clean and friendly atmosphere. The inn is walking distance to all downtown shops and restaurants, town beach, ferry terminals, and public transportation. The charming Balcony Room boasts a private flowery balcony and a private bathroom in the room. Stenciled bordered walls and original wide pine flooring.

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Popular amenities for Oak Bluffs boutique hotels

Wi-Fi

Free parking on premises

Air conditioning

Family-friendly boutique hotels

A comfortable sleeping area features a spacious bed with smooth linens. Beside the bed, a small wooden table with two stools is visible. The wall is adorned with a sign reading 'Vineyard Haven', adding a local touch to the decor.

5.0 out of 5 average rating, 4 reviews

Vineyard Harbor Motel - Unit 227

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A spacious room features a modern bed with a white quilt and decorative pillows. A small desk with two chairs is positioned against the wall, accompanied by a refrigerator and air conditioning unit. Nautical-themed decor and a round mirror enhance the ambiance.

4.63 out of 5 average rating, 97 reviews

Boutique motel w/ private beach, steps from ferry

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A view of the harbor features several yachts docked along a wooden pier. Colorful flowers in a planter are positioned in the foreground. The sky is overcast, creating a calm ambiance over the water.

4.78 out of 5 average rating, 103 reviews

Vineyard Harbor - Harbor View Unit 224

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A view from inside the condo showcases a round wooden table with white chairs. Through the large windows, a sandy beach is visible, adorned with blue beach chairs and boats anchored in the calm water under a clear sky.

4.73 out of 5 average rating, 62 reviews

Vineyard Harbor - Unit 108

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A bright room features a queen bed covered with a light quilt, accompanied by a twin daybed. A small wooden table and chair provide a workspace. Wall art and framed pictures decorate the space, with a window allowing natural light and an air conditioning unit for comfort.

4.75 out of 5 average rating, 68 reviews

Vineyard Harbor - Unit 223

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A well-lit room features two blue upholstered armchairs positioned beside a light-colored side table. A floor lamp stands nearby, while a mirror reflects the space. In the background, a bed dressed in a floral comforter is complemented by framed artwork on the walls.

4.4 out of 5 average rating, 48 reviews

Vineyard Harbor - Unit 234

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A sandy beach area is depicted, featuring lounge chairs positioned near the water's edge. Boats are docked at a nearby marina, and calm waters reflect a clear blue sky. The scene is framed by a wooden deck, enhancing the beachside atmosphere.

4.48 out of 5 average rating, 46 reviews

Vineyard Harbor - Unit 238

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Boutique hotels with a patio

A welcoming common area features a mix of comfortable seating, including patterned chairs and a spacious sofa. A large coffee table is centered on a textured area rug, with natural light streaming through expansive glass doors. Decorative plants and rustic wooden beams enhance the warm ambiance.

4.5 out of 5 average rating, 22 reviews

THE FRANKLIN HOTEL ~NEW Pet Friendly Standard King

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A spacious bed is adorned with white linens and a decorative pillow featuring a floral design. The wall above the headboard displays an arrangement of framed artwork, including photographs and colorful prints, contributing to the room's artistic ambiance.

4.78 out of 5 average rating, 18 reviews

MORGAN HOTEL ~ Standard Queen Room ADA w/ Bathroom

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4.72 out of 5 average rating, 29 reviews

MORGAN HOTEL ~ Standard King w/ Private Bathroom

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A stylish bedroom is highlighted by a four-poster bed with a white comforter and decorative pillows. Large windows allow natural light to illuminate the space, complemented by framed artworks on the nearby walls. A small side table adds functionality beside the bed.

4.25 out of 5 average rating, 4 reviews

MORGAN HOTEL ~ David Healey Suite w/ private bath

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MORGAN HOTEL ~ Ocean view King Room w/ Verandah

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THE FRANKLIN HOTEL ~NEW Pet Friendly Luxury King

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Other boutique hotel holiday rentals

4.89 out of 5 average rating, 54 reviews

Porch Room 1 queen bed

LocationFamilyCleanliness

4.91 out of 5 average rating, 57 reviews

Balcony Room at the Tivoli Inn

ValueLocationQuiet

4.95 out of 5 average rating, 20 reviews

Three bedrooms for travel group/excellent location

LocationFamilyCheckout

4.7 out of 5 average rating, 138 reviews

Hotel room in Woods Hole

Treehouse Lodge, Canopy style rooms

ValueLocationAccuracy

4.93 out of 5 average rating, 84 reviews

Park Side Queen Room @ Frederick William House

LocationComfortAccuracy

4.86 out of 5 average rating, 7 reviews

A cozy inn room is presented with a spacious bed and a light blue sofa. A wooden table holds a remote control and a small vase with a flower. Natural light streams through the window covered by striped valances, illuminating soft blue walls.

Hotel room in Chilmark

Astilbe Room @ Beach Plum Inn

LocationFamilyBreakfast

The Victorian gingerbread house features a wrap-around porch adorned with lace-like trim. Flowering plants provide a colorful contrast against the wooden exterior, while a second-floor balcony overlooks the street. This charming structure captures the essence of classic seaside architecture.

4.91 out of 5 average rating, 44 reviews

Sunny-Side Room at the Tivoli Inn

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