Top 16 Cool and Unusual Hotels in Martha’s Vineyard 2022

The elegant, upscale and beautiful Massachusetts island located in the Atlantic Ocean, just south of Cape Cod is a much-loved vacation resort, day-tripper destination and celebrity haunt. Accessible only by boat or air, it’s a quiet, uncommercialised bubble of peace and quaint scenic beauty filled with pretty harbor towns, fine chef-driven independent restaurants, striking lighthouses, lush green farmland, miles of biking and hiking trails and world-class sandy beaches.

From cozy and intimate boutique inns to hip and ultra-creative, here are the best cool and unusual hotels in Martha’s Vineyard, Massachusetts (in no particular order)...

1. The Sydney – a colorful, kitsch, and cool boutique place to stay in Martha’s Vineyard

The Sydney - a colorful, kitsch, and cool place to stay in Martha’s Vineyard2

The Sydney - a colorful, kitsch, and cool place to stay in Martha’s Vineyard The Sydney - a colorful, kitsch, and cool place to stay in Martha’s Vineyard1

A hip and trendy hotel that blends luxury, style and service, all located in the heart of Downtown Edgartown, just moments from the dock, the wonderful restaurants, galleries and other attractions that make this such a fantastic place to visit.

Spread across two historic buildings, Captain’s House, a stunning example of 19th century New England clapboard housing, and a cape style main building. White wicker, neutral tones and modern wood finishes give a contemporary feel throughout, with rooms spacious and comfortable.

Breakfast is high-quality and delicious, and an in-house restaurant provides casual dining at other times, while there is a patio and fire pit to enjoy in the evenings.

2. The Christopher – one of the most Instagrammable hotels in Martha’s Vineyard

The Christopher - one of the most Instagrammable hotels in Martha's Vineyard2

Trendy and hip hotel in Martha's Vineyard

A boutique inn of just 15 rooms, The Christopher brings eclectic design to its stunning period property and offers a unique experience for every guest.

With bright, bold colors, modern furniture and classic New England features, few can match this contemporary hotel for a luxurious, unforgettable experience.

A garden gives plenty of space to enjoy the sea breeze and the warm evening weather, while a buffet breakfast is minimalist, but always delicious and everything you need to fuel your day’s adventure.

Despite all the quirks and unique design, this is a thoroughly modern hotel, and as such is a bit different to the traditional experience you would get in the area.

One for those looking for more luxury and convenience from their stay in Martha’s Vineyard.

3. Summercamp – a cool, trendy and fun hotel with ocean views perfect for partying Millenials and Gen Zs

Summercamp - a trendy hotel Summercamp - a trendy hotel2

Hip boutique hotel in Martha's Vineyard

Summercamp - a trendy hotel1

A historic hotel that gets its name from the former use of the area as a summer camp destination for the Methodist Church, situated in a property that has been welcoming travelers since 1879.

This quirky party hotel embraces modern luxury but adds in nostalgic touches such as Twister and Ping Pong in the game room, snacks in the camp canteen, a real memory for anyone who spent time at summer camp.

Rooms at this cool Martha’s Vineyard hotel are light and elegant, with a contemporary design that embraces natural materials and subtle colors.

This amazing hotel can make you feel like a kid again, but with concierge services,  luxury rooms, stunning balconies and more, it offers the complete modern hotel experience as well.

4. The Edgartown Inn – a unique, and very Instagrammable historic inn that offers concierge services

The Edgartown Inn - a unique and historic innThe Edgartown Inn - a unique and historic inn1 The Edgartown Inn - a unique and historic inn2

A historic hotel housed in a period property originally built in 1798 and owned by a whaling captain. Counting John F. Kennedy among its many famous guests over the years, it sits in a convenient location in Downtown Edgartown with restaurants and attractions all within easy walking distance.

Rooms at this chic boutique hotel feature colonial furniture, including genuine antiques, while brass plaques tell you of the famous guests who have used each room.

Bright and airy, the rooms have period style but offer luxurious accommodation. Continental breakfasts offer quality food, and service is always exceptional.

5. Edgar Hotel Martha’s Vineyard, Ascend Hotel Collection – a cute boutique-style hotel that is within close proximity to the Lighthouse Beach

Edgar Hotel Martha's Vineyard, Ascend Hotel Collection - a boutique-style hotel Edgar Hotel Martha's Vineyard, Ascend Hotel Collection - a boutique-style hotel1 Edgar Hotel Martha's Vineyard, Ascend Hotel Collection - a boutique-style hotel2

Bringing the style and elegance of old time New England alongside the comfort and convenience of modern living, this is a boutique hotel of impeccable style and fantastic service.

Quality furnishings provide luxurious surroundings in every room, with a nautical theme in keeping with the history of the area, creating light, welcoming spaces to enjoy.

In-house dining comes from the Town Bar and Grill, offering casual dining with locally sourced ingredients for a wonderful dining experience, whether inside watching sports or out on the patio for a meal under the stars.

6. The Richard – a charming boutique hotel that offers a romantic atmosphere

The Richard - a charming boutique hotel The Richard - a charming boutique hotel1 The Richard - a charming boutique hotel2

Standing right on Main Street at the heart of Edgartown, this boutique hotel is set inside a wonderful period property that began life as home for a ship’s captain.

Eventually becoming an inn during its long history, The Richard has been subject to a recent renovation and is now a 16 room, contemporary hotel that gives period New England style and modern luxury.

Rooms at this cool Martha’s Vineyard hotel are mostly monochrome, with touches of color to add a cosmopolitan feel, while evenings spent outside by the fire remind you of the wonderful location and its natural beauty.

Close to restaurants and entertainment, if you are visiting Edgartown and want something a little more modern to come home to, this is the perfect luxury hotel.

7. Lambert’s Cove Inn & Resort – an Insta-worthy upscale 18th-century resort located in a rural setting

Lambert's Cove Inn & Resort - an upscale 18th-century resort Lambert's Cove Inn & Resort - an upscale 18th-century resort1 Lambert's Cove Inn & Resort - an upscale 18th-century resort2

Sitting at the heart of 8-acres of lush forest and manicured gardens, Lambert’s Cove Inn is a luxury hotel offering the island retreat experience and a tranquil life among stunning surroundings.

The main building began life as a farmhouse, first built in 1790, and period touches remain everywhere, while the 25 guest rooms all incorporate modern touches that make for a relaxing stay.

An award-winning hotel property, there is a wonderful on-site restaurant for casual dining, cycling trails and complimentary bicycles, a working farm area with egg-laying chickens as well as Alpacas, an outdoor pool and access to a nearby private beach. It’s the perfect place to unwind and recharge.

8. Winnetu Oceanside Resort at South Beach – easily one of the coolest resorts to stay in Martha’s Vineyard perfect for families

Winnetu Oceanside Resort at South Beach - easily one of the coolest resorts to stay in Martha’s Vineyard Winnetu Oceanside Resort at South Beach - easily one of the coolest resorts to stay in Martha’s Vineyard1 Winnetu Oceanside Resort at South Beach - easily one of the coolest resorts to stay in Martha’s Vineyard2

Named as one of the top 25 resorts in New England by Conde Nast Traveler, Winnetu is a stunning modern hotel and resort that features a contemporary style with light and spacious rooms that deliver comfort for all the family. An in-house restaurant offers relaxed dining and fresh local ingredients.

Outdoor swimming pools, tennis courts, yoga classes and a fitness center keep you busy, while kids and separate teen activities take care of your family too, making this luxury hotel the perfect family getaway.

You are just a few steps from the warm sands and crystal-clear water of South Beach too, and all the fun the beach and water sports bring. A fantastic destination, it has everything you need in one place.

9. The Morgan Hotel Martha’s Vineyard – a contemporary design hotel that is within walking distance from the beach

The Morgan Hotel Martha's Vineyard - a contemporary and designed hotel The Morgan Hotel Martha's Vineyard - a contemporary and designed hotel1

Sitting within walking distance of Seaview Beach, Ocean Park and other Oak Bluffs attractions, this is a modern hotel with an easy, elegant style that makes you feel at home.

Having been a lodging establishment since 1873, this quirky hotel has a timeless beauty, the patina of age blending with the modern facilities and design touches everywhere you look.

Each room is different, offering comfort, space and style, and the beauty of the location is that it puts you on the doorstep of a wealth of fine restaurants offering every choice of cuisine you can imagine.

A great way to experience Oak Bluffs, The Morgan Hotel lets you take a trip back in time without sacrificing any modern luxury.

10. Charles and Charles MV – a quirky-chic bed & breakfast that offers complimentary bicycles for guests to explore the area

Charles and Charles MV - a quirky-chic bed & breakfast Charles and Charles MV - a quirky-chic bed & breakfast1 Charles and Charles MV - a quirky-chic bed & breakfast2

Just 15 minutes’ walk from Main Street, Charles and Charles is a boutique hotel of just 6 rooms, each with its own unique style. They offer contemporary comfort with period design touches, creating a wonderfully indulgent space to relax and enjoy this fabulous region.

Bicycles are available to use to explore the island, they even provide helmets, smartphone maps and some detailed local knowledge to help you find quiet and secluded areas off the beaten track to enjoy your vacation. 

Within easy reach of the diverse range of restaurants and other eating options, this is a unique hotel that gives you something different for your stay.

11. Harbor View Hotel – a hip upscale hotel located in the heart of historic Edgartown

Harbor View Hotel - an upscale hotel located in the heart of historic Edgartown Harbor View Hotel - an upscale hotel located in the heart of historic Edgartown1 Harbor View Hotel - an upscale hotel located in the heart of historic Edgartown2

A 117-room luxury hotel and resort sat overlooking the picture-perfect harbor area and surrounded by manicured gardens and lush greenery, Harbor View Hotel has been welcoming guests to its landmark building for over 130 years, since 1891.

Since that beginning, this historic hotel has played host to movie stars, world leaders, athletes and more, and it is easy to see why.

Rooms are majestic, blending period touches with contemporary luxury, two high-quality dining options on site and plenty more within easy access, a heated pool and private beach cabanas, a fitness center, yoga classes and complementary bicycles give you plenty to do while you are enjoying the super service.

12. The Oak Bluffs Inn – a fun and funky hotel perfect for partying Millennials and Gen Zs

The Oak Bluffs Inn - a fun and funky hotel perfect for partying Millennials and Gen Zs1 The Oak Bluffs Inn - a fun and funky hotel perfect for partying Millennials and Gen Zs1 The Oak Bluffs Inn - a fun and funky hotel perfect for partying Millennials and Gen Zs2

The distinctive profile of the Oak Bluffs Inn is part of the landscape, having first appeared in 1870. First taking guests at the turn of the century, this historic hotel has provided exceptional accommodation for well over 100 years and continues to do so today.

 Just 10 rooms make up this boutique hotel, each with period style, space and comfort, all just 4 minutes walk from the beach and the wonderful downtown area with its restaurants and attractions.

If you want hotel luxury but apartment independence, Oak Bluffs Inn gives you everything you need, along with a healthy dose of coastal charm.

13. Narragansett House – a charming historic-themed Victorian inn with quirky-chic unique decor

Narragansett House - a historic Victorian inn Narragansett House - a historic Victorian inn1 Narragansett House - a historic Victorian inn2

With its bold purple walls and pink doors, Narragansett House is a historic hotel that stands out from the crowd. Built in 1870 as a guest house, you can’t fail to see history in every room.

But while the décor brings that period style to life, each room also delivers bright, contemporary feel and comfort too.

Looking out over the ocean, the views are spectacular, and with just 12 rooms, this boutique hotel really looks after you. Continental breakfasts are included, with the option to eat outside on the deck as you take in that fresh morning air. Sit back, relax and watch the world go by.

14. Hob Knob – a 19th-century eco-friendly gothic hotel that provides stylish accommodations and an onsite spa

Hob Knob - a 19th-century eco-friendly gothic hotel Hob Knob - a 19th-century eco-friendly gothic hotel1 Hob Knob - a 19th-century eco-friendly gothic hotel2

A spectacular upscale hotel that has been providing a unique experience for guests for close to 100 years, Hob Knob offers superb hospitality, modern amenities and wonderful period décor.

Sitting in the vibrant Downtown area of Edgartown, close to the restaurants, museums and attractions and within walking distance of the shore, it is perfectly placed for any trip.

A luxury hotel that features antiques and fine art mixed with modern amenities to create supremely comfortable accommodation, this resort also includes a spa, and offers organized excursions with local experts to help you make the most of your trip to the island.

It’s a unique experience, a trip back in time and the best of modern hotels, in one package.

  • To book, check prices or availability for Hob Knob

15. Inkwell Beach Cottage – an oceanfront B&B close to popular historic landmarks

Inkwell Beach Cottage - an oceanfront B&B Inkwell Beach Cottage - an oceanfront B&B1 Inkwell Beach Cottage - an oceanfront B&B2

Sit back on the porch and admire the ocean view as you watch the world drift by. There is nothing finer than a luxury hotel experience to help you rest and recharge, and at Inkwell Beach Cottage, you have it all.

Boldly colored and with a nautical theme that befits the beachside location, each room offers its own individual style that makes every stay a pleasure.

Sit on the broad front porch and watch the stars in the evening, or enjoy your breakfast in the fresh morning air, and explore the wonderful surroundings, whether a walk down the sandy beach or enjoying the museums, stores and restaurants that are everywhere around you.

A relaxing option where life is just that little bit slower for your relaxation.

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