These inns and resorts take old Cape Cod charm and add modern conveniences
Technically, Cape Cod is a peninsula, but the opening of the Cape Cod Canal in 1914 created a water line with mainland Massachusetts, uniting the Cape with its neighbors, real islands, Martha’s Vineyard and Nantucket as a trio of vacation destinations. Each is a different experience, but they all come 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
The Chatham Bars Inn, which opened in 1914, is located on the southeast elbow of Cape Cod on the Atlantic side on 25 acres of waterfront property that includes its own 400-meter private beach. The main inn, which is surrounded by 37 clapboard cottages with suites of various sizes, includes the large, bright South Lounge. It includes a fireplace and board games for colder weather, plus a wraparound porch – perfect for a relaxing lunch overlooking the water.
For dinner, the sumptuous Stars offers dishes inspired by produce from the inn’s 2.4-acre farm. For deep relaxation, the spa offers a steam room and sauna, a full range of treatment and cosmetic services, and a private zen garden with a heated pool and adult-only cabanas.
Hotel with harbor view | Edgartown, Martha’s Vineyard
Harbor View Hotel in Edgartown on Martha’s Vineyard – photo courtesy Shannon Shipman
This chic 1891 resort on Lighthouse Beach, half a mile from downtown Edgartown, includes a main inn with rooms with water views; the Governor Mayhew Building overlooks the garden and the seasonal outdoor pool and cabanas; and The Cottages, which are apartment-size suites with kitchens.
The main inn’s wraparound porch overlooks the harbor and beach of Chappaquiddick Island, and the lobby lounge swaps the view for a cozy fireplace. The Roxy Pool Bar and Bettini Club are perfect for drinks and casual dining, and the Bettini, decorated in dramatic cherry red, teal, and reclaimed natural wood, is one of the Vineyard’s finest restaurants.
Harbor view Nantucket | Nantucket
Waters Edge Cottage in Harborview Nantucket – Photo courtesy Linda Laban
Within walking distance of Nantucket’s shopping and dining, this secluded beachfront enclave of 11 luxury cedar clapboard cottages offers self-catering with fully equipped kitchens and dining rooms. Each cottage is different, ranging from a cozy studio fisherman’s apartment to a renovated four-bedroom barn.
Most have decks and outdoor showers. Harbourview Nantucket, which winds around a central lawn leading to the beach, functions like a hotel with daily housekeeping. Although there is no restaurant or bar, the concierge will shop and fill your fridge.
Wequassett Resort and Golf Club | Harwich, Cape Cod
Wequassett Resort and Golf Club in Harwich on Cape Cod – photo courtesy Linda Laban
Located on peaceful Pleasant Bay, this resort has one of the best golf clubs in the United States – Cape Cod National Golf Club – on its doorstep. But there’s so much more to enjoy at this Mid Cape Lodge, which is surrounded by cedar shingles of various designs.
There is also tennis, two pools and the spacious rooms and extravagant suites with terraces and fire pits. Enjoy dinner or a drink at Thoreau’s, housed in a 19th-century captain’s house that had been moved by Brewster, or the main Twenty-Eight Atlantic restaurant, where a locally inspired menu offers vibrant flavors – even at breakfast.
The Charlotte Inn | Edgartown, Martha’s Vineyard
The Terrace Restaurant at The Charlotte Inn in Edgartown on Martha’s Vineyard – photo courtesy Linda Laban
This posh old inn is packed with Victoriana and knick-knacks that are deliberately reminiscent of a bygone era. But interestingly, the front living room is officially the Edgartown Art Gallery, which, in addition to its antiques, also exhibits new art by local artists. As a member of the Relais & Châteaux organization, everything from food to furnishings is of the highest quality.
A fireplace seat in the mahogany-paneled Green Room is perfect for pre-dinner cocktails at The Terrace restaurant, a bright conservatory with potted palms, and more art and artifacts. The rooms are all individually decorated with incredible antiques, reproductions, and vintage trickery, from Victorian collar boxes to vintage steamer suitcases.
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 just as natural as the most comfortable and elegant ambience. An adults-only retreat, the Wauwinet stands on the site of the original hotel, which opened in 1875.
In addition to 32 guest rooms and suites in the main hotel, there are three cottages, including the beachfront three-bedroom Anchorage House. Guests can enjoy activities on both ocean and Nantucket Bay private beaches, play tennis, enjoy a free harbor and cheese lesson, and dine at world-class Topper’s, which features a seasonally inspired menu featuring local produce and seafood.
Winnetu Oceanside Resort | Edgartown, Martha’s Vineyard
Edgartown on Martha’s Vineyard – Photo courtesy of iStock / DenisTangneyJr
This extremely family-friendly resort offers fun for all ages, from cocktails on The Dunes Deck overlooking the grounds or a luxurious spa treatment to giant chess, horse riding on an antique jitney or relaxing on the pool deck. The sandy South Beach sits on 11 acres, flanked by farmland and the Atlantic Ocean, just a quarter of a mile away. And Winnetu’s water taxi or shuttle van takes guests to Edgartown, about a 10-minute drive.
Accommodation ranges from townhouses to studio suites. The kitchenettes have a full refrigerator and a huge coffee maker with organic fair trade coffee. Meanwhile, The Dunes restaurant serves up sophisticated American standards and New England seafood alongside live music in the evenings.
The Coonamessett | Falmouth, Cape Cod
The Coona Messette in Falmouth, Cape Cod – photo courtesy Linda Laban
Part of Lark Hotels, a New England-based design-focused boutique hotel chain, this motel with cottage-style studio suites and a main inn with a ballroom and open lobby combines the charm of Cape Cod on the outside and modern amenities on the inside.
Rooms have a modernist oceanfront design, including sofas with wood and burlap accents, and sisal rugs. The continental breakfast is served free in the lobby, and Eli’s Tavern’s has a menu that’s just as focused on ingredients as the stylish rooms, all of which can be enjoyed in the pretty wood-paneled room or on the secluded terrace overlooking beautiful Jones Pond .
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 Linda Laban
Located on the less touristy western tip of the island, the pretty Menemsha Inn and its neighboring sister town, Beach Plum Inn, overlook Vineyard Sound in the distance. The area is still rough and natural, and because Chilmark is a dry city with no public alcohol, there is no night life other than dinner and the spectacular sunset.
The food in the inn takes place in the excellent restaurant of the Beach Plum. Choose from delightful rooms at Menemsha’s Carriage and Tea Houses or one of the freestanding cabins, which come complete with kitchens, decks, fireplaces, and uninterrupted water views.
Lands End Inn | Provincetown, Cape Cod
Lands End Inn in Provincetown on Cape Cod – photo courtesy Linda Laban
This spectacular, clapboard former Queen Anne style private home in Provincetown’s West End sits on top of Gull Hill and offers soothing views over the harbor. Today it is a luxury B&B with 18 sumptuously furnished guest rooms, including some cottages with a terrace. The living rooms are exquisitely furnished in a high Victorian style and antique, vintage or just cool lamps are scattered throughout the property.
The large veranda overlooking the magnificent wild rose garden is another beautiful feature. Only children over 10 years of age are allowed to be more concentrated than retreats for adults. The inn is just a pleasant short walk from the art galleries, restaurants and famous seasonal nightlife of downtown P-town.