13 Hotels

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1

Charlotte Inn

$$$$ | 27 S. Summer St., Edgartown, Massachusetts, 02539, USA

From the moment you walk up to the dark-wood Scottish barrister's desk to check in at this regal 1864 inn, you… Read More

B&B/Inn · Historical · Romantic · Service · Design · Sophisticated · Central


2

Harbor View Hotel and Resort

$$$$ | 131 N. Water St., Edgartown, Massachusetts, 02539, USA

The centerpiece of this historic hotel is a gray-shingled, 1891 Victorian building with wraparound veranda and… Read More

Resort · Business · Service · Views · Casual Chic · Casual · On the beach · Family


3

Hob Knob

$$$$ | 128 Main St., Edgartown, Massachusetts, 02539, USA

This 19th-century Gothic Revival boutique hotel blends the amenities and service of a luxury property with the… Read More

B&B/Inn · Green · Service · Pet Friendly · Casual Chic · Quiet · Central · Fodor's Splurge · Fodor's Choice


4

Winnetu Oceanside Resort

$$$$ | 31 Dunes Rd., Edgartown, Massachusetts, 02539, USA

A departure from most properties on the island, the contemporary Winnetu—styled after the grand multistory res… Read More

Resort · Service · Views · Casual Chic · Lively · Remote · Fodor's Choice · Family


5

Crocker House Inn

$$$ | 12 Crocker Ave., Vineyard Haven, Massachusetts, 02568, USA

This casual 1890 farmhouse-style inn is tucked into a quiet lane off Main Street, minutes from the ferries and… Read More

B&B/Inn · Views · Casual Chic · Casual · Near the beach


6

Mansion House

$$$ | 9 Main St., Vineyard Haven, Massachusetts, 02568, USA

There has been a hostelry on this Main Street site just above Vineyard Haven Harbor since 1794. In 2003, it wa… Read More

Hotel · Business · Views · Pet Friendly · Casual Chic · Casual · Central


7

Outermost Inn

$$$ | 81 Lighthouse Rd., Aquinnah, Massachusetts, 02535, USA

This rambling, sun-filled inn by the Aquinnah Cliffs stands alone on acres of moorland, a 10-minute walk from… Read More

B&B/Inn · Romantic · Views · Casual Chic · Quiet · Remote · Fodor's Splurge


8

Twin Oaks Inn

$$$ | 28 Edgartown Rd., Vineyard Haven, Massachusetts, 02568, USA

On a half acre of landscaped lawn within walking distance of the ferry, this family-friendly inn is part class… Read More

B&B/Inn · Casual Chic · Lively · Central · Family


9

Edgartown Inn

$$ | 56 N. Water St., Edgartown, Massachusetts, 02539, USA

The inside of the former home of whaling captain Thomas Worth still evokes its late-18th-century origins. In f… Read More

B&B/Inn · Historical · Local Flavor · Casual · Central · Fodor's Value


10

Lambert's Cove Inn, Farm & Restaurant

$$ | 90 Manaquayak Rd., off Lambert's Cove Rd., West Tisbury, Massachusetts, USA

A narrow road winds through pine woods and beside creeper-covered stone walls to this posh, handsomely designe… Read More

B&B/Inn · Romantic · Service · Pet Friendly · Casual Chic · Quiet · Countryside · Fodor's Splurge · Fodor's Choice


11

Madison Inn

$$ | 18 Kennebec Ave., Oak Bluffs, Massachusetts, 02557, USA

While this stylish little inn doesn't have the high prices of nearby hotels, it does have all the amenities yo… Read More

B&B/Inn · Casual Chic · Casual · Near the beach · Fodor's Value


12

Pequot Hotel

$$ | 19 Pequot Ave., Oak Bluffs, Massachusetts, 02557, USA

In this casual cedar-shingle inn on a tree-lined street, the first floor has a wide porch with rocking chairs—… Read More

B&B/Inn · Casual Chic · Casual · Near the beach · Fodor's Value


13

Greenwood House

$ | 40 Greenwood Ave., Vineyard Haven, Massachusetts, 02568, USA

A low-key B&B on a quiet lane around the corner from Vineyard Haven's public library, the Greenwood House… Read More

B&B/Inn · Romantic · Casual Chic · Quiet · Central · Fodor's Value

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