Martha's Vineyard, United States

The Sydney

Price per night from$379.00

Price information

If you haven’t entered any dates, the rate shown is provided directly by the hotel and represents the cheapest double room (including tax) available in the next 60 days.

Prices have been converted from the hotel’s local currency (USD379.00), via, using today’s exchange rate.


Whale of a time


Elegant Edgartown

Real estate on Martha’s Vineyard may be almost 100 per cent more expensive than anywhere else in the USA, but luckily you can borrow the Sydney for the night instead. This boutique bolthole is in Edgartown, the pretty island’s most picturesque corner and once the hub of the whaling industry (hence the historic captain’s houses). Lots of the harbor town’s restaurants are a short stroll away, as are its cute boutiques and smart galleries. Back at your home-from-home, there’s iced coffee on tap to enjoy by the fire pit, a bottle shop over the road to perk up the hotel’s mixer station and pre-dinner treats put out daily. 

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Some Murdick's Fudge


Photos The Sydney facilities

Need to know


22, including two suites.


11am. Earliest check-in, 4pm.


Double rooms from £328.42 ($416), including tax at 9.7 per cent.

More details

Rates usually include breakfast.


The Lark Suite is ADA-approved for guests with mobility issues.

Hotel closed

The seasonal Sydney is shuttered up from October until April.

At the hotel

Free WiFi throughout, fire pit, coffee and water station at reception. In rooms: waffle bathrobes, air-conditioning, minibar, USB sockets, TV and Lather bath products.

Our favourite rooms

The rooms all share the same bright, breezy decor, with uplifting accents such as bold striped rugs, floral blinds and matching cushions, and nautical nods like seashells starring in the artworks.

Packing tips

The summer crowd is a well-heeled one, but they know how to cut loose and switch to island time – though a few smart options for the fancier restaurants wouldn’t go amiss. There are steamers in the rooms ready to tackle any suitcase-created creases.


The ‘Martha’ part of the island’s moniker is down to a British explorer, who named it after his daughter, having crossed the Atlantic in 1602 (he’s also responsible for Cape Cod, which he so-christened for its fish).


All ages are welcome at the Sydney and there are connecting rooms available, but there are no special facilities for children.

Food and Drink

Photos The Sydney food and drink

Top Table

Out by the fire pit on the patio making new friends.

Dress Code

As long as you’re not wearing whites after Labor Day, you’ll be fine.

Hotel restaurant

There’s no restaurant at the hotel, but lots of Edgartown’s esteemed eateries are nearby. Breakfast is served in the lounge and out on the patio. It’s a selection of small plates (chia puddings, zucchini bread, blueberry muffins), which you can keep going with until you’re suitably sated. The front-desk area also offers refreshments in the form of various taps, dispensing still and sparkling water, kombucha and cold-brew coffee 24 hours a day; and afternoon-tea treats at 3pm. 

Hotel bar

In addition to the cold drinks and coffee flowing freely at reception, there’s a bottle shop called Vintage over the road, where you can select your bottle of choice after a chat with the helpful owner John. The Sydney doesn’t have a liquor licence but you’ll be able to imbibe John’s wares, with a little help from the mixer bar set up every afternoon at the hotel, with things like cranberry juice, ginger ale, bitters and margarita mixers ready to improve your beverage of choice.

Last orders

Breakfast is served between 8am and 10am.


Photos The Sydney location
The Sydney
22 Winter Street Martha's Vineyard
United States

The Sydney is far from its Antipodean namesake and actually in Martha’s Vineyard, in the centre of Edgartown and opposite Chappaquiddick Island.


Martha’s Vineyard has its own regional airport, but most international arrivals will touch down in Boston. From the city’s Logan International Airport, the drive south to the island, via the car ferry, should take two-and-a-half hours.


You won’t need wheels for exploring Edgartown, but if you have come by car there’s limited parking at the hotel. Spaces cost $50 a day and will need to be booked in advance.


Ferries connect Cape Cod's Hyannis port on the Massachusetts mainland with the islands of Martha’s Vineyard and Nantucket.

Worth getting out of bed for

The Sydney is in the centre of Edgartown, whose narrow streets, art galleries and charming boutiques you can easily explore on foot. Staff will send you off to the beach with a Sunflow seat (basically a chair in a backpack) – the nearest in walking distance is the Lighthouse Beach, but the team is also enamoured of South Beach. They will also be able to equip you with borrowed bicycles, a Jeep or even your own sailboat and skipper. For a classic Martha’s Vineyard experience, head to the other side of the island to see the cliffs and Gay Head Lighthouse at Aquinnah, before locating a shack in the fishing village of Menemsha for some lobster rolls (try Larsen’s or Menemsha Fish Market).


Local restaurants

Helpfully located right next-door to the Sydney, L’Etoile is one of the most popular restaurants on the island so be sure to make a reservation. Also within rolling-home distance of the hotel is Alchemy, which celebrates the Atlantic bounty with dishes such as scallop linguine, yellowfin tartare with crispy artichokes, crab and asparagus salad, and shrimp fritters. For turf as well as surf, 19 Raw has an oyster bar, a sub-menu of crudos and ceviches, and also moonlights as the Vineyard’s finest cast-iron steakhouse.

Local cafés

For acai bowls, smoothies and general health-giving breakfasts and lunches, Among the Flowers supplies all the clean-eating you need, with a bloom-covered patio to enjoy it on, of course. Rosewater will prepare picnics, dispense wine, beers and spirits, and good vibes only to set you up to have a truly nice day. And it may require pre-caffeination effort, but you’ll be glad you located this café at the back of a bookshop – Behind the Bookstore serves coffee, breakfast and lunch.

Local bars

For cocktails made even better by a view of the harbor, the Atlantic is the sundowner spot for you. More mixology mastery awaits at Rockfish, which is also famous for its flatbreads in case you’re in need of some alcohol-absorbing. Or try not to sing like a fisherman at the Seafood Shanty overlooking Edgartown Harbor.


Photos The Sydney reviews

Anonymous review

Every hotel featured is visited personally by members of our team, given the Smith seal of approval, and then anonymously reviewed. As soon as our reviewers have returned from this high-on-the-charm hotel in Massachusetts and unpacked their saltwater taffy and Murdick’s Fudge, a full account of their island break will be with you. In the meantime, to whet your wanderlust, here's a quick peek inside the Sydney in Martha’s Vineyard…

If Martha’s Vineyard is holiday heaven, then Edgartown – a walkable quarter with historic captain’s houses (a relic from the island’s whaling days), galleries, boutiques and brilliant restaurants – in the island’s east is peak summer-holiday paradise, especially if you’re staying at the Sydney. Edgartown was the Vineyard’s first settlement, founded in 1642 with a prosperous whaling industry ensuing a century or so later. 

In the middle of the action, the Sydney is a quaint, cosy hotel, with a fire pit for sociable guests, coffee and kombucha on tap in reception, and beach chairs and bicycles to borrow to improve an already idyllic vacation. The rooms at the Sydney have playful pops of pattern and colour, with artfully mismatched cushions, lampshades, headboards and wallpaper. There’s a restaurant (one of the best on the island, no less) just next door, and many of Edgartown’s finest eateries are within walking distance, too. The Sydney may be on Winter Street but it’s always summer on Martha’s Vineyard.

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Price per night from $379.00