Boutique hotel vacation rentals in Oak Bluffs

Find and book unique boutique hotel rentals on Airbnb

Top-rated boutique hotel rentals in Oak Bluffs

Guests agree: these boutique hotel rentals are highly rated for location, cleanliness, and more.

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Superhost

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

4.78 out of 5 average rating, 74 reviews

THE FRANKLIN HOTEL~NEW Pet friendly Standard Queen

KeithRating, 5 stars2 weeks ago

We had a fantastic stay at The Franklin Hotel! The location is perfect. Just a short walk to everything in Edgartown, from great restaurants to the waterfront. The room was spotless, the check-in process was seamless with easy electronic key access, and the shared common area was cozy, stylish, and perfect for relaxing after a day of exploring. We were visiting for my partner’s birthday, and they went above and beyond by surprising us with a lovely bottle of wine. That personal touch really made our stay feel special. Thank you, Elijah! Highly recommend this spot if you’re looking for a clean, comfortable, and centrally located place to stay on the island. We’ll definitely be back!

Guest favorite

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.

Hotel room in Falmouth

4.95 out of 5 average rating, 22 reviews

Deluxe Black King Suite @ Frederick William House

VickiRating, 5 stars7 months ago

This was such a fun visit. Jeanette made us feel right at home. The house is a treasure. The outdoors have so many areas to sit and visit. We loved being able to walk on the trail and have dinner and walk to the shuttle. Very comfortable and cozy stay!

A well-maintained pool area features a refreshing blue pool surrounded by a sleek white deck. Comfortable lounge chairs are arranged beside the pool, complemented by elegant planters filled with lush greenery. Large umbrellas provide shade over cushioned seating against a backdrop of a white fence.

Hotel room in Tisbury

5 out of 5 average rating, 22 reviews

Luxurious & Comfortable Queen Room in B&B

JodeeRating, 5 stars17 months ago

Charles’ place was pure heaven! Every conceivable kindness awaits guests. When we checked in he gave us home made from scratch cookies that were in a word, glorious. He gave us a bottle of wine. The towels are on a towel warmer. The linens are fine crisp, cool and beautiful. Every last detail from the coffee maker and the European bidet to the lighting and the bicycles and helmets available to guests speak volumes about the class and comfortable, laid-back elegance of this absolutely perfect Airbnb experience. Charles even has an alarm clock that projects the time on the ceiling. A hamlet of exquisiteness. My new home away from home.

A small dining table is positioned near a window, offering a view of a serene waterfront. Two wooden chairs flank the table, which holds a decorative bowl. Sunlight illuminates the space, highlighting the soft blue tones of the water and sky.

Hotel room in Tisbury

4.76 out of 5 average rating, 97 reviews

Vineyard Harbor - Harbor View Unit 224

AnneRating, 5 stars12 months ago

I was concerned finding a convenient and open spot “off season” was going to leave me with few options. I was glad to find Lory’s spot and it was just as described. I had work obligations and my husband was able to stay and enjoy the 2nd floor deck and watch the activity in the harbor. He thoroughly enjoyed it. While coffee was available in the reception area I like to walk in the morning and the Black Lab Bakery was very close and open early. We would stay again.

Guest favorite

A wrap-around porch is featured, showcasing white rocking chairs and a wicker table with a small vase. The porch is bordered by green grass and shaded by trees, creating a serene outdoor space for relaxation.

Hotel room in Oak Bluffs

4.95 out of 5 average rating, 38 reviews

Sunny-Side Room at the Tivoli Inn

JanetRating, 5 stars8 months ago

Had a lovely stay here! Loved the outdoor shower! Comfy bed and pillows. Lisa was so kind and put my beach towels on the dryer before I left, and gave us excellent dinner and lunch recommendations. Will definitely stay again when I’m on the area.

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Popular amenities for Oak Bluffs boutique hotel rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly boutique hotels rentals

Superhost

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.

Hotel room in Falmouth

4.85 out of 5 average rating, 47 reviews

Luxury SeaSide King Suite, Frederick William House

DonnaRating, 5 stars4 months ago

We stayed a few nights and the inn was quaint and cozy. Perfectly located to restaurants and shops. Our host Jeanette was friendly and very helpful. The continental breakfast was served in the cutest dining area and her homade coffee cake was delicious.

Superhost

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.

Hotel room in Falmouth

4.87 out of 5 average rating, 23 reviews

Harborside G King Suite @ Frederick William House

KimberlyRating, 5 stars4 days ago

Incredibly well maintained home and grounds. Jeanette was a wonderful host and made us feel right at home!

Guest favorite

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.

Hotel room in Falmouth

4.95 out of 5 average rating, 22 reviews

Deluxe Black King Suite @ Frederick William House

VickiRating, 5 stars7 months ago

This was such a fun visit. Jeanette made us feel right at home. The house is a treasure. The outdoors have so many areas to sit and visit. We loved being able to walk on the trail and have dinner and walk to the shuttle. Very comfortable and cozy stay!

Guest favorite

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.

Hotel room in Falmouth

4.91 out of 5 average rating, 64 reviews

Glendale Petite @ Frederick William House

CaraRating, 5 stars1 month ago

We loved our stay here! Jeanette was a kind and thoughtful host. The space was clean and exactly what we paid for. The included breakfast was a delight. We’d definitely stay here again.

Guest favorite