Boutique hotel vacation rentals in Oak Bluffs

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

DonnaRating, 5 stars6 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.

Two golden-brown quiches are presented, featuring a flaky crust and topped with thinly sliced zucchini and tomatoes. The surface is lightly browned and slightly bubbly, indicating a freshly baked texture. The second quiche, placed behind the first, is partially visible.

4.95 out of 5 average rating, 22 reviews

Deluxe Black King Suite @ Frederick William House

VickiRating, 5 stars9 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!

4.92 out of 5 average rating, 71 reviews

Park Side Queen Room @ Frederick William House

PatriciaRating, 5 stars2 months ago

Absolutely love our stay! The white room was beautiful and exactly as described! The bed was extremely comfortable and I loved the lounging chair for reading. The outside balcony was wonderful to sit on. The bike/walking bath was very accessible and provided a great afternoon of walking. The Knob recommendation was breath taking! Thank you for your morning conversations and getting to know you!! Definitely would recommend this bed and breakfast!

The exterior of the Tivoli Inn is showcased, highlighting its Victorian Gingerbread architecture. A charming wrap-around porch features rockers and is adorned with flowers, while balconies are visible on the upper level, framed by lush greenery and trees in the surrounding area.

4.91 out of 5 average rating, 11 reviews

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.

Top guest favorite

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, 38 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.

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*

4.78 out of 5 average rating, 91 reviews

A welcoming entrance showcases a covered porch with a sitting area featuring a red rocking chair. Neatly trimmed hedges and a small sculpture enhance the front garden, while the wooden steps lead to a door framed by sidelights and a lantern above.

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.

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, 75 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.

A welcoming porch area features white rocking chairs and a glass-topped wicker table. The wooden floor is painted in a soft green hue. Lush greenery is visible in the background, providing a serene setting for relaxation.

4.89 out of 5 average rating, 45 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.

A wooden picnic table is positioned on a deck overlooking the harbor. The scene captures a serene sunset with hues of orange and pink lighting the sky, while several boats are anchored nearby, creating a peaceful waterfront atmosphere.

Hotel room in Tisbury

4.74 out of 5 average rating, 85 reviews

Vineyard Harbor - Harbor View Unit 237

Vineyard Harbor offers comfortable rooms, a private beach and an incredible location. We are situated on the harbor in Vineyard Haven within walking distance to the ferry, unique shops, great restaurants and perfectly placed to explore the island. Vineyard Harbor is the perfect location from which to explore Martha’s Vineyard.

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Popular amenities for Oak Bluffs boutique hotel rentals

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly boutique hotels rentals

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.

4.85 out of 5 average rating, 47 reviews

Luxury SeaSide King Suite, Frederick William House

DonnaRating, 5 stars6 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.

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.

4.87 out of 5 average rating, 23 reviews

Harborside G King Suite @ Frederick William House

KimberlyRating, 5 stars1 month ago

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

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.

4.95 out of 5 average rating, 22 reviews

Deluxe Black King Suite @ Frederick William House

VickiRating, 5 stars9 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 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.

4.92 out of 5 average rating, 71 reviews

Park Side Queen Room @ Frederick William House

PatriciaRating, 5 stars2 months ago

Absolutely love our stay! The white room was beautiful and exactly as described! The bed was extremely comfortable and I loved the lounging chair for reading. The outside balcony was wonderful to sit on. The bike/walking bath was very accessible and provided a great afternoon of walking. The Knob recommendation was breath taking! Thank you for your morning conversations and getting to know you!! Definitely would recommend this bed and breakfast!

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.

4.91 out of 5 average rating, 64 reviews

Glendale Petite @ Frederick William House

CaraRating, 5 stars2 months 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.

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Boutique hotels rentals with a patio

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 out of 5 average rating, 3 reviews

MORGAN HOTEL ~ David Healey Suite w/ private bath

TracyRating, 5 stars33 months ago

Great place! Very clean in an excellent location. Host very helpful. Definitely recommend.

A well-appointed sleeping area features a spacious bed with a textured white coverlet. Dark-colored doors contrast against the light walls, with a kitchenette area visible in the background. A mounted television and large window allow for natural light to fill the room.

5 out of 5 average rating, 6 reviews

MORGAN HOTEL ~ Standard Queen w/ wet bar

ChrisRating, 5 stars7 months ago

We really enjoyed our stay and Jerron was a great host. Would absolutely stay here again.