We review the top 10 best luxury hotels on the Cape & Islands. Our list includes Harbor View Hotel, Carpe Diem Guesthouse & Spa, Chatham Bars Inn, Hob Knob, Ocean Edge Resort, and Golf Club, Red Inn, The Charlotte Inn, Vineyard Square Hotel & Suites, Wequassett Resort and Golf Club, Winnetu Oceanside Resort.
Cape Cod, Martha’s Vineyard, and the smaller Elizabeth Islands, and Nantucket County all form part of Cape Cod and the Islands. The islands south of the Cape, much like Cape Cod itself, were originally whaling and trading areas that have more recently evolved into resort destinations, where wealthy families, celebrities, and tourists spend the summer months.
We review the top 10 best luxury hotels on the Cape & Islands. Wherever you decide to stay, on the Cape & Islands, or elsewhere, book via our luxury travel concierge. We offer free upgrades, free breakfasts, and free perks at hotels, including the Four Seasons, Hyatt, Ritz-Carlton, InterContinental, and more.
Typically, our free benefits at luxury hotels include:
- Room upgrade to next category
- Complimentary breakfast for two per bedroom
- Complimentary Welcome Gift
- $100 USD equivalent Hotel experiential credit per room per stay
- Early check-in / late check-out (subject to availability)
- Complimentary Wi-Fi
1. Harbor View Hotel
Harbor View Hotel is located in Martha’s Vineyard and is surrounded by miles of beaches in the storybook village of Edgartown.
Just 7 miles off the coast of Massachusetts, this exclusive 117-room resort provides guests with the perfect Martha’s Vineyard vacation oasis with top-tier dining and breathtaking views of the Edgartown Harbor. This iconic hotel is only steps away from boutiques, art galleries, beaches, and sunset cruises.
The unprecedented 2020 renovation of Harbor View Hotel offers beautifully redesigned spaces. Within the rooms, every last detail of your stay has been thoughtfully curated. The plush robe you love still hangs in the closet. Molton Brown toiletries mesmerize the senses. Wi-Fi and wireless speakers mean a soothing playlist for your slumber in Frette linens. At sunrise, fire up the Nespresso coffee machine, then explore the isle in a Mercedes Benz or bicycle. Work out in the fully-stocked gym before a dip in the outside heated saltwater pool.
In terms of dining, Paris has The Ritz. Venice has Harry’s Bar. And Martha’s Vineyard has Bettini. This is the place to see and be seen and eat more fabulously than anywhere on the island. Overseen by culinary director Hart Lowry, whose provenance includes James Beard award-winning restaurants in Boston and Manhattan, Bettini is understated glitz at its finest. Top-tier American cuisine and island-sourced fresh oysters plucked out of the Atlantic that morning… Think Grilled Cracked 2lb Lobster with poached market vegetables, champagne & caviar beurre blanc and Seared Wagyu Strip Steak with black garlic rub, bourbon-soy butter, and herb emulsion. Further upping the fun factor is Roxy Pool Bar, a sun-kissed, al fresco dining experience full of sophisticated cocktails, tapas, comfy couches, fire pits, and fun.
Honored four separate times as “Best Place for a Wedding” by two leading industry publications, The Harbor View also offers an unrivaled array of indoor and outdoor settings, complete with stunning ocean and garden views. The historic building enchants couples and corporate groups. Friends love to pow-wow in the chic and sophisticated atmosphere of The Roxana. Families gather at cozy reunion dinners in stand-alone Captain’s Cottages. And for the glitterati, there is only one choice on the island: the unparalleled Presidential Skyhouse.
2. Chatham Bars Inn
Chatham Bars Inn is New England’s Grand Oceanfront Resort. The kind of place where affluent travelers from yesteryear used to spend their summers. Where they splashed in the surf, played golf in the tangy sea air, took afternoon tea on the wide veranda overlooking panoramic ocean vistas, and dined on the best New England cuisine, featuring fresh-from-the ocean seafood. More recently, this iconic hotel was lovingly restored to its original grandeur so that the more modern traveler can enjoy these same simple pleasures.
Chatham Bars Inn sits on 25 acres of beautifully landscaped grounds and sandy ocean beaches. The hotel offers a rich variety of guestroom styles and types. Ranging from a historic guestroom in the Main Inn to an ocean view cottage two-bedroom master suite complete with fireplaces, steam shower, dining area, and wet bar, there is room to meet any desire.
Many families enjoy selecting an entire cottage to meet their needs or connecting rooms, which provide convenience and privacy. Nearly all of the 217 guestrooms vary in size and décor. From bright summer ocean colors to warm Adirondack furnishing, each has been decorated in a way to remind you where you are, Cape Cod.
Work on your golf swing or tennis swing, take a cooking class or take a walk on the beach, splash in the ocean or soak in the whirlpool, ride on a boat or ride a bike or you can try the new Spa at Chatham Bars Inn which is available exclusively for hotel guests. Other activities include a Fitness center, tennis courts, a croquet court, outdoor pool, putting green, golf, and a private beach.
3. Wequassett Resort and Golf Club
Wequassett Resort and Golf Club, which is a member of Preferred Hotels and Resorts, draws visitors from the world over to its New England setting overlooking Pleasant Bay and the Atlantic. Wequassett’s pristine white buildings and tidy clapboard cottages are nestled on sea-facing bluffs and 27 acres of gardens, marshes, and woodlands. Guest rooms, many with water views, are decorated in elegant country style; dining across five venues is polished and posh. The neighboring exclusive Cape Cod National Golf Club allows play for resort guests. Tennis, water sports, and a children’s club round out the many available activities.
Decorated beautifully to match the Cape Cod cottage architecture, this elegant yet understated- resort is an idyllic destination offering one hundred and twenty guest rooms. The views of Pleasant Bay are simply spectacular from the three waterfront restaurants, as well as from the pool area.
The summer Jazz festival series, which takes place throughout July and August, is not to be missed, and the live music down on the new Pleasant Bay Terrace is the ideal locale to savor a “liBAYtion” or light summer supper. The quintessential Cape Cod experience is captured with traditional Clambakes, tennis, boating, world-class golf, and beaching activities aplenty.
4. Ocean Edge Resort and Golf Club
Ocean Edge Resort and Golf Club is more than a Cape Cod beach resort. It provides experiences as diverse as the accommodations that guests call home.
The Mansion at Ocean Edge offers high-end refined accommodations. From the Presidential Bay Collection’s breezy villas to the Mansion Wing’s upscale guestrooms, this AAA Four Diamond-rated property has a room for every taste and the amenities to match.
Perhaps the highlight of these larger accommodations is their access to all that Ocean Edge has to offer. Fitness, dining, and Bay Pines Private Beach are all just steps from your front door.
5. Red Inn
The Red Inn in Provincetown, Cape Cod, was built in 1805 on beautiful Provincetown Harbor. The Red Inn has welcomed guests since 1915, including President and Mrs. Theodore Roosevelt, celebrities, and dignitaries. Today The Red Inn is known around the world for offering premier accommodations in a spectacular setting.
The hotel’s most recent renovation, in 2011, was designed to highlight The Red Inn’s old-world ambiance, unparalleled views, multiple fireplaces, beamed ceilings, and wide-board pine floors, creating a relaxing environment of understated sophistication.
The Inn features three beautifully appointed guest rooms, three spacious suites, and two luxurious private residences, all with waterfront decks and breathtaking views of Provincetown Harbor and Cape Cod Bay.
6. Vineyard Square Hotel & Suites
Located in a prime spot in the heart of the historic downtown Edgartown where all of the best restaurants and shops are found, Vineyard Square Hotel & Suites offers a charming Martha’s Vineyard getaway filled with warm hospitality and comfortable accommodations. Walk outside this boutique Edgartown hotel and delight in the gourmet restaurants, quaint shops, and vibrant arts scene of Martha’s Vineyard just steps from the front door.
Guests who stay here receive continental breakfast daily, complimentary bikes to use (the preferred mode of transportation around town), an on-site salon and day spa, as well as a beautiful front porch complete with more than a dozen rocking chairs ideally situated for some great people watching.
7. Hob Knob
The eco-chic luxury boutique hotelHob Knob, has played host to JFK and is just a few minutes walk from the heart of Edgartown. Here, classic style and sophistication meet superb comfort and convenience in downtown Edgartown, one of New England’s most picturesque coastal villages. Picnic lunches, beach chairs, and umbrellas are available via the guest concierge, as well as local farm-to-table breakfast and afternoon tea. A highlight is the 27’ Boston Whaler with a captain available to reserve for fishing trips, sunset cruises, or some island touring from the water.
8. Winnetu Oceanside Resort
Winnetu is the only hotel located just above the shoreline of popular South Beach. 1-4 bedroom suites, private cottages as well as private rental homes ranging from 2-5 bedrooms are available to book. Having one of the most popular beaches on the island at your doorstep is a serious perk, plus the hotel offers a complimentary shuttle to and from downtown, a tennis club, yoga, multiple pools, and children’s programs.
9. The Charlotte Inn
Entering its fifth decade in business, the Charlotte Inn offers the attention to detail, service and quality that Relais & Chateau properties such as this one have come to be known for. The Edwardian décor with modern amenities bestows the elegance of a bygone era. Flanked by historic whaling captain homes, the setting is quintessential Edgartown. There is also the bonus of Hermès and Bulgari toiletries.
10. Carpe Diem Guesthouse & Spa
Carpe Diem Guesthouse & Spa is a Provincetown Inn, with a tranquil Zen garden. Elegant sitting areas and quiet corners invite guests to read, have good conversations, or just to listen to the sound of numerous water features or the meditative gurgle of the fish pond’s little waterfall. During the summer months, guests can have breakfast at the large outside table under the wisteria arbor or gather there for the hotel’s Happy Hour in the afternoon.
The eighteen rooms at Carpe Diem Guesthouse are all unique in their style, taking inspiration from the concept of a New England sea captain journeying to Asia, creating a wonderful fusion of two styles. The color scheme is creamy with tones of gray and a historic naval blue. Accents of Asian and nautical style blend to create a classic and elegant environment.
Guests who stay here also get complimentary access to the facilities at Namaste Spa, Provincetown’s best-rated spa, along with a cooked-to-order breakfast and evening wine and cheese hour, which offers an opportunity to meet the other guests.
Note: Benefits offered correct at the time of writing but may be amended at discretion of the vendor. Posts may be sponsored by the proprietor or brand being appraised. All opinions remain our own & are in no way influenced.