Technically, Cape Cod is a peninsula, but the opening of the Cape Cod Canal in 1914 created a water border with mainland Massachusetts, unifying the Cape with its neighbors, true islands, Martha's Vineyard and Nantucket as a trio of vacation spots. Each is a different experience, but all are stocked with boutique inns and fabulous resorts.
Chatham Bars Inn | Chatham, Cape Cod
Chatham Bars Inn in Chatham on Cape Cod — Photo courtesy of Chatham Bars Inn
Situated on Cape Cod’s southeastern elbow on its Atlantic Ocean side, Chatham Bars Inn, which opened in 1914, is set on 25 waterside acres that include its own quarter-mile private beach. The main inn, which is surrounded by 37 shingled cottages containing suites of varying sizes, includes the big, bright South Lounge. It includes a fireplace and board games for colder weather, as well as a wraparound veranda – perfect for a relaxing lunch overlooking the water.
For dinner, the sumptuous Stars offers dishes inspired by produce from the inn’s eight-acre farm. For some deep relaxation, The Spa has a steam room and sauna, a full range of treatment and aesthetician services, and a private Zen garden with adults-only heated pool and cabanas.
- Chatham Bars Inn
Harbor View Hotel | Edgartown, Martha’s Vineyard
Harbor View Hotel in Edgartown on Martha's Vineyard — Photo courtesy of Shannon Shipman
Dating to 1891, this chic resort on Lighthouse Beach, about half a mile from Edgartown’s center, includes a main inn with water view rooms; the Governor Mayhew building overlooking the garden and seasonal outdoor pool and cabanas; and The Cottages, which are apartment-sized suites with kitchens.
The main inn’s wraparound veranda overlooks the harbor and Chappaquiddick Island’s beach, and the lobby lounge swaps views for a cozy fireplace. The Roxy Pool Bar and Bettini Club are perfect for drinks and casual dining, and Bettini, which is decorated in dramatic cherry red, teal and reclaimed natural wood, is among the Vineyard’s best restaurants.
- Harbor View Hotel
Harborview Nantucket | Nantucket
Water's Edge cottage at the Harborview Nantucket — Photo courtesy of Linda Laban
With Nantucket’s shopping and dining only a few minutes' walk away, this secluded, beachside enclave of 11 cedar-shingled luxury vacation cottages offers self-catering with fully equipped kitchens and dining rooms. Each cottage is different, ranging from a cozy studio fisherman’s abode to a four-bedroom renovated barn.
Most have decks and outdoor showers. Harborview Nantucket, which wraps around a central lawn leading to the beach, operates like a hotel, with daily housekeeping. Though there isn’t a restaurant or bar, the concierge will shop and fill your fridge.
- Harborview Nantucket
Wequassett Resort and Golf Club | Harwich, Cape Cod
Wequassett Resort and Golf Club in Harwich on Cape Cod — Photo courtesy of Linda Laban
Set on peaceful Pleasant Bay, this resort includes one of the finest golf clubs in the United States – the Cape Cod National Golf Club – right on the doorstep. But there’s so much more to enjoy on this Mid Cape lodge, which is surrounded by cedar-shingled cottages of various designs.
There’s also tennis, two pools and the spacious rooms and extravagant suites, which have patios and fire pits. Enjoy dinner or drinks in Thoreau’s, set in an 1800s sea captain’s house that was moved from Brewster, or the main restaurant, Twenty-Eight Atlantic, where a locally inspired menu offers vibrant flavor pairings – even at breakfast.
- Wequassett Resort and Golf Club
The Charlotte Inn | Edgartown, Martha's Vineyard
The Terrace restaurant at The Charlotte Inn in Edgartown on Martha's Vineyard — Photo courtesy of Linda Laban
This genteel old inn is packed with Victoriana and knickknacks, deliberately recalling a bygone era. But, interestingly, the front sitting room is officially the Edgartown Art Gallery, displaying new art from local artists amongst its antiques. As a member of the Relais & Châteaux organization, everything is top-notch, from food to furnishings.
A seat by the fireplace in the mahogany-paneled Green Room is perfect for cocktails before dinner in The Terrace restaurant, a bright conservatory with potted palms and even more art and artifacts. Rooms are all individually furnished with incredible antique, reproduction and vintage bric-a-brac, from Victorian collar boxes to vintage steamer trunks.
The Wauwinet | Nantucket
The Wauwinet on Nantucket — Photo courtesy of White Elephant Resorts
As a member of the exclusive Relais & Châteaux collection, top service and fine cuisine are a standard, along with the most comfortable and beautifully designed surroundings. The Wauwinet, an adults-only retreat, stands on the site of the original hotel opened in 1875.
Along with 32 guest rooms and suites in the main hotel, there are three cottages, including the three-bedroom, beach-side Anchorage House. Guests may enjoy activities on private beaches on both the ocean and Nantucket Bay, tennis, a complimentary port and cheese hour, and dining in the top-notch Topper’s, which boasts a seasonally inspired menu focused on local produce and seafood.
- The Wauwinet
Winnetu Oceanside Resort | Edgartown, Martha’s Vineyard
Edgartown on Martha's Vineyard — Photo courtesy of iStock / DenisTangneyJr
This extremely family-friendly resort has fun for all ages, from cocktails on The Dunes’ deck overlooking the grounds or a sumptuous spa treatment to playing giant chess, riding on an antique jitney or relaxing on the pool patio. Set on 11 acres, flanked by farm land and the Atlantic Ocean, sandy South Beach is a delightful quarter of a mile walk away. And Winnetu’s water taxi or shuttle van ferries guests into Edgartown, about a 10-minute journey.
Accommodations range from townhouses to studio suites. The kitchenettes include a full fridge and giant coffee maker with organic Fair Trade coffee. Meanwhile, The Dunes restaurant offers refined American standards and New England seafood, in addition to live music in the evenings.
The Coonamessett | Falmouth, Cape Cod
The Coonamessett in Falmouth on Cape Cod — Photo courtesy of Linda Laban
Part of Lark Hotels, a high-design-focused, New England-based boutique hotel chain, this motel-style spread of cottage-y studio suites, plus a main inn building with a ballroom and open plan lobby, mixes Cape Cod charm on the outside and modern amenities on the inside.
Rooms have a modernist seaside design, including wood- and burlap-accented couches and sisal rugs. Continental breakfast is served complimentary in the lobby, and Eli's Tavern’s has a menu as ingredient-oriented as the rooms are stylish, all to be enjoyed in the handsome wood-paneled space or on the secluded deck overlooking beautiful Jones Pond.
- The Coonamessett
Menemsha Inn & Cottages and the Beach Plum Inn | Chilmark, Martha’s Vineyard
Menemsha Inn & Cottages and the Beach Plum Inn in Chilmark on Martha's Vineyard — Photo courtesy of Linda Laban
Located in the less touristy western tip of the island, the pretty Menemsha Inn and its adjacent sister spot, the Beach Plum Inn, overlook Vineyard Sound in the distance. The area is still raw and natural, and because Chilmark is a dry town where alcohol isn’t served publicly, there’s no nightlife beyond dinner and the spectacular sunset.
Dining at the inn takes place at the Beach Plum’s excellent restaurant. Choose from delightful rooms in Menemsha’s Carriage and Tea Houses, or one of its standalone cabins, which come complete with a kitchen, decks, fireplaces and open views to the water.
- Menemsha Inn & Cottages
Lands End Inn | Provincetown, Cape Cod
Lands End Inn in Provincetown on Cape Cod — Photo courtesy of Linda Laban
This spectacular, shingled Queen Anne-styled onetime private home in Provincetown’s West End sits at the top of Gull Hill, giving soothing views over the harbor. Now a luxury B&B, there are 18 sumptuously furnished guest rooms, including some cottages with patios. The sitting rooms are exquisitely furnished in high Victorian style, and antique, vintage or just plain cool lamps sit throughout the property.
The large veranda overlooking the delightful wild rose-laden garden is another gorgeous feature. More focused as an adult retreat, only children over 10 are allowed. The inn is a pleasant short walk from downtown P-town’s art galleries, restaurants and famed seasonal nightlife.