Escape to the Bay State—18 Dreamy and Romantic Getaways in Massachusetts

Massachusetts is one of those states that somehow has it all. It's home to one of the dreamiest coasts in the country (hello, Cape Cod), is a hub of culture and history, and offers some seriously gorgeous fall leaf peeping and warm-weather activities. That said, romantic getaways in Massachusetts are as diverse as the state itself.

Whether you two lovebirds are craving a stay at a cozy, picturesque inn tucked in the Berkshires, dreaming of an oceanside retreat along the Cape, or have your heart set on charming city stays in Boston, the Bay State is ready to deliver.

Romantic Getaways In This Article:

• Romantic Weekend Getaways in Massachusetts
• Romantic Inns in Massachusetts
• Romantic Hotels in Massachusetts
• Romantic Bed-and-Breakfasts in Massachusetts
• Romantic Fall & Winter Getaways in Massachusetts
• Romantic Spring & Summer Getaways in Massachusetts

Romantic Weekend Getaways in Massachusetts

From luxurious spa weekends to nature-filled escapes, there's a romantic weekend getaway in Massachusetts for every couple, occasion and time of year.

The Wauwinet, Nantucket, Massachusetts

Photo: The Wauwinet

You can't say no to a weekend with bae in Nantucket, which is only a short flight or ferry from the mainland. This adults-only icon sits at the far end of Nantucket, past the buzz of town and into total tranquility. "The Wauwinet is all about sexy seclusion a la wine at sunset, waterfront serenity and long bike rides to empty beaches," says Anne Poole, travel expert and founder of Bon Vivant Luxury Travel. "There's also an award-winning on-site restaurant, Topper's, that makes staying put very tempting."

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Things to Do: Explore Coskata-Coatue Wildlife Refuge, visit the Whaling Museum, bike the scenic island trails and enjoy shopping downtown.

120 Wauwinet Road, Nantucket, MA 02584

4.4 Star Rating | Read Reviews

Hotel AKA Back Bay, Boston, Massachusetts

Photo: Hotel AKA Back Bay

A weekend in Boston is twice as nice when you get to retreat back to one of the city's most luxurious hotels. The 225-room Hotel AKA Back Bay has historic roots (it was once home to Boston's Police Department Headquarters), but has since been redesigned by the acclaimed Selldorf Architects. Guest rooms feature custom oak furnishings, Scandi-inspired wares, spa-like bathrooms, spacious seating areas and urban views. There's also a gorgeous restaurant on the property (The Berkeley Bistro and Bar), or you can sleep in and order room service. Or do both!

Things to Do: The hotel is situated within walking distance of the boutiques on Newbury Street, as well as the picturesque Commonwealth Avenue Mall. It's also about a five-minute drive away from the Public Garden and Theater District.

154 Berkeley Street, Boston, MA 02116

4.5 Star Rating | Read Reviews

Miraval Berkshires, Lenox, Massachusetts

Photo: Miraval Berkshires

For couples craving reconnection (with each other and themselves) Miraval Berkshires is the ultimate wellness escape, and it goes far beyond a basic spa weekend. "It's mind-body magic in the Berkshires: yoga under the trees, floating meditation, hikes, equine therapy, sound baths and farm-to-table meals that somehow feel indulgent and virtuous," Poole says. She adds, "A digital detox is strongly encouraged, making the whole experience more intimate." It's located about two and a half hours from either Boston or NYC, and is beautiful from spring through fall.

Things to Do: You'll want to soak up as much time on-property as possible. The expansive 220-acre preserve has all sorts of activities planned each day, including guided forest hiking, beekeeping, meditations and more.

55 Lee Road, Lenox, MA 01240

4.3 Star Rating | Read Reviews

Romantic Inns in Massachusetts

Picture your couple's vacation now: strolling hand in hand through cobblestone streets, sipping wine at historic vineyards, and catching a sunrise over the Atlantic before cozying up for your stay in a romantic Massachusetts inn.

Inn on Boltwood, Amherst, Massachusetts

Photo: Inn on Boltwood

The historic Inn on Boltwood is a boutique hotel that fuses historic New England charm with all the likings of modern comfort. It's a quintessential romantic retreat that puts you two right in the heart of Massachusetts' Pioneer Valley. We love the intimate scale (only 49 rooms) and curated design choices that are connected to the original architecture. And fun fact: The historic ambiance is elevated by the Inn's connection to Shirley Graham Du Bois, an author, playwright, composer and civil rights activist who lived at the inn while teaching at Amherst College in the '70s.

Things to Do: The property is super close to the Amherst College campus, so stroll through historic grounds and visit a variety of museums. The surrounding Pioneer Valley also features numerous hiking trails, antique shops, and local farms that make for some pretty dreamy day trips.

30 Boltwood Avenue, Amherst, MA 01002

4.5 Star Rating | Read Reviews

Nobnocket Boutique Inn, Vineyard Haven, Massachusetts

Photo: Nobnocket Boutique Inn

Nobnocket Boutique Inn is a stunning stay nestled on two acres of gardens and woodland within Martha's Vineyard. The Arts and Crafts-style property was originally built in 1908, and has been updated over the years to add modern features, like large picture windows for sweeping garden views, open living spaces and original artwork. Whether staying for a quick overnight or a few days, it's a serene and immersive experience that really dials up the romance.

Things to Do: Venture downtown to explore the quaint shops and stunning harbor, catch an early morning or sunset sail/stroll along Owen Park Beach, and don't miss a visit to nearby West Chop for a peaceful, scenic drive together.

60 Mount Aldworth Road, Vineyard Haven, MA 02568

5.0 Star Rating | Read Reviews

The Williams Inn, Williamstown, Massachusetts

Photo: The Williams Inn

Located in picturesque Williamstown—the Northern Berkshires region of the state—The Williams Inn offers a super-romantic, upscale stay. It's overflowing with New England everything: hospitality, cuisine, and even that fusion of farmhouse-meets-contemporary aesthetic. The three-story property is intimate with 64 spacious rooms, a quaint lobby, and a signature on-site restaurant (The Barn) that serves up local, seasonal food.

Things to Do: The inn's prime Spring Street location makes it easy to enjoy all that Williamstown has to offer, including charming shops, local dining, and arts and culture at Williams College, The Clark Art Institute and MASS MoCA.

101 Spring Street, Williamstown, MA 01267

4.7 Star Rating | Read Reviews

Romantic Hotels in Massachusetts

New England is brimming with all sorts of charming stays, but if you're looking for plush amenities and full-service romance, these standout hotels are all winners.

The Newbury Boston, Boston, Massachusetts

Photo: The Newbury Boston

For a touch of that Wes Anderson-inspired aesthetic, book a hotel stay at The Newbury Boston. Opened in 1927 as one of the first Ritz-Carlton properties in the US, the 16,000-square-foot property has since been meticulously maintained and updated. From Public Garden strolls to cozy toasts in The Street Bar to dinner overlooking the twinkling city lights at Contessa, we love that there are plenty of romantic things to do together within the hotel itself, too. (Psst! Look into the Newbury's Romance Package, which sets you up for a weekend escape, including a guest room or suite, a welcome champagne amenity, breakfast for two and late check-out.)

Things to Do: Just steps away from the hotel, couples can stroll through the charming Public Garden, ride the city's iconic Swan Boats, or browse luxury boutiques and art galleries.

1 Newbury Street, Boston, MA 02116

4.7 Star Rating | Read Reviews

Kimpton Marlowe Hotel, Cambridge, Massachusetts

Photo: Kimpton Marlowe Hotel

Nestled on the banks of the Charles River in Cambridge's vibrant Kendall Square, the Kimpton Marlowe Hotel lends a serene, romantic getaway. Guests are welcomed by Celeste, a striking 25‑foot kinetic armillary sculpture in a charming courtyard, and the interior dazzles even more with renovated guest rooms and suites. The property also has bonus amenities, like a 24-hour fitness center, evening wine hours and is pet-friendly. Definitely check out the on-site restaurant, Bambara Kitchen and Bar.

Things to Do: Mosey along the Charles River Esplanade, rent a kayak for a paddle with skyline views, and explore the Museum of Science. For food, grab a cozy dinner in Kendall Square, or cross the bridge for nightlife and theaters in downtown Boston.

25 Edwin H. Land Boulevard, Cambridge, MA 02141

4.4 Star Rating | Read Reviews

Wequassett Resort & Golf Club, Harwich, Massachusetts

Photo: Wequassett Resort & Golf Club

Wequassett Resort and Golf Club is the quintessential romantic waterfront escape on Cape Cod, tucked away in Harwich, Massachusetts. Just two hours from Boston, the 27-acre estate feels worlds away from city life, offering sweeping views of Pleasant Bay and Chatham Harbor that set the stage for a chic yet deeply intimate getaway. Hit the private sandy beaches hand-in-hand, sip on tasty cocktails on seaside terraces, or retreat to elegant guest rooms and private cottages with cozy fireplaces and soaking tubs perfect for unwinding together.

Things to Do: Take a sunset sail around the Cape, bike through nearby Chatham's charming streets lined with boutiques and galleries, or book a couples' golf or tennis lesson at the resort's world-class facilities.

2173 Head of the Bay Road, Route 28, Harwich, MA 02645

4.5 Star Rating | Read Reviews

Romantic Bed-and-Breakfasts in Massachusetts

You'll feel like you're living in a dreamy rom-com waking up in these romantic B&Bs in Massachusetts. A tasty breakfast in the morning seals the deal.

Howarth House Bed-and-Breakfast, Fitchburg, Massachusetts

Photo: Howarth House Bed-and-Breakfast

With just three suites, the Howarth House Bed-and-Breakfast is our most intimate stay on this list of romantic Massachusetts getaways. The property, just a short drive from Boston, truly strikes the perfect balance between intimate serenity and upscale comfort. Of course, your stay includes a delicious made-to-order gourmet breakfast each morning using fresh and high-quality ingredients (including eggs laid on the property's farm). Guests can also enjoy a variety of freshly made baked goods, snacks and drinks throughout the day at their own leisure.

Things to Do: Spend the morning or afternoon wandering through the diverse collections of the Fitchburg Art Museum. For an outdoor retreat, check out scenic trails at Flat Rock Wildlife Sanctuary.

81 Ross Street, Fitchburg, MA 01420

5.0 Star Rating | Read Reviews

The Cornell Inn, Lenox, Massachusetts

Photo: The Cornell Inn

The Cornell Inn is neatly tucked within the cultural core of the Berkshires and features three storied estates, including one dating all the way back to 1777, another from 1888, and a character‑filled Carriage House whispered to have been a Prohibition‑era speakeasy. Refined comfort is of the utmost importance here (seriously, the property looks like it's out of a home design magazine), and guests also get to enjoy daily gourmet breakfasts.

Things to Do: Check out the town's postcard-perfect streets, visit the historic Lenox Library (housed in a former 19th‑century courthouse), and tour The Mount, which is Edith Wharton's beautifully preserved estate and gardens.

203 Main Street, Lenox, MA 01240

4.7 Star Rating | Read Reviews

Brook Farm Inn, Lenox, Massachusetts

Photo: Brook Farm Inn

Also located in Lenox, Brook Farm Inn is a wow-worthy Victorian bed-and-breakfast that was erected in 1882. With 15 uniquely appointed guest rooms (including an accessible carriage house and two‑room suite options), each is equipped with private baths, cozy furnishings, and thoughtful character touches that lean into the history. You two can start your day off on the right foot with full, happy bellies thanks to a chef-prepared, seasonal, plated breakfast.

Things to Do: Cozy up together with a romantic walk in downtown Lenox, poking around boutique shops, cafés and restaurants. Kennedy Park isn't too far away, either, for those who want to do some hiking.

15 Hawthorne Street, Lenox, MA

4.9 Star Rating | Read Reviews

Romantic Fall & Winter Getaways in Massachusetts

When the leaves transform into gold and copper—or the snow begins to fall—Massachusetts transforms into a storybook setting. These romantic retreats are perfect for cozying up by the fire, watching the foliage blaze or the snow drift gently outside your window.

Raffles Boston, Boston, Massachusetts

Photo: Raffles Boston

Did someone say Boston leaf peeping? New on the scene and already stealing hearts, Raffles Boston delivers on cosmopolitan glamour and is easy to reach from just about anywhere in the Northeast. "The vibe is polished and plush, with moody lighting, marble everything and a quietly luxurious feel throughout," Poole says. "Grab a table at Long Bar—outside if the weather's playing nice—for skyline views and champagne toasts, or stay in bed and order room service, which is divine." She also says not to skip the spa; it's sleek, seductive, and perfect for a couple's treatment before a dip in the indoor pool.

Things to Do: Warm up with a stroll through Copley Square and the historic Boston Public Library, browse stylish boutiques along Newbury Street, or sip hot, seasonal cocktails in one of the area's intimate lounges. For a festive touch, visit the holiday lights in the Public Garden or take in sweeping city views from the Skywalk Observatory at the Prudential Center.

40 Trinity Place, Boston, MA 02116

4.2 Star Rating | Read Reviews

The Red Lion Inn, Stockbridge, Massachusetts

Photo: The Red Lion Inn

The Red Lion Inn is a treat year-round, but we're calling it out for the uber cozy vibes it brings once the weather chills. The two-century-old property offers four types of lodging experiences across its iconic Main Inn, Maple Glen, and unique houses in the village, with no two rooms the same. It's located in the Berkshires, which is a plus all on its own, and the property also does an excellent job with its experiences. From magic shows in its historic parlor to a grand piano playing tunes to murder mystery weekends, there's always something fun on the docket.

Things to Do: Wander hand in hand through storybook New England charm, browse indie galleries and cozy cafés while soaking in the timeless ambiance that inspired Norman Rockwell himself.

30 Main Street Stockbridge, MA 01262

4.0 Star Rating | Read Reviews

The Salem Inn, Salem, Massachusetts

Photo: The Salem Inn

Salem, Massachusetts, has to be one of the premier cities to visit in the United States in autumn. It's definitely got those spooky, Halloween-season vibes on lock, and it also offers coastal charm, rich history and cozy fall date spots. As for where to stay, The Salem Inn is a fitting choice. This historic property features 40 guest rooms in three historic homes, each named after a key part of the city's storied history.

Things to Do: Explore Salem's historic streets on a candlelit ghost tour, visit the Salem Witch Museum or browse the autumn markets at the Salem Common. In autumn, don't miss the Haunted Happenings festivities, where the entire town transforms with parades, costumed visitors and spooky seasonal charm.

7 Summer Street, Salem, MA 01970

4.2 Star Rating | Read Reviews

Romantic Spring & Summer Getaways in Massachusetts

As the weather warms, the Bay State sparkles with blooming gardens, ocean breezes and sun-soaked adventures. These romantic spring and summer getaways are ideal for everything from coastal strolls to countryside picnics—or maybe even a Massachusetts proposal!

Sea Crest Beach Resort, North Falmouth, Massachusetts

Photo: Sea Crest Beach Resort

Nestled along the peaceful shores of Cape Cod, Sea Crest Beach Resort is just a two-hour drive from Boston. That makes it the perfect coastal escape from the city, and an easy train ride from anywhere on the East Coast. It's actually the Upper Cape's only beachfront property, and it has truly refined the romance experience. Whether you two are canoodling and sipping wine at sunset or sharing a quiet morning walk along Old Silver Beach, it's the perfect spring and summer retreat.

Things to Do: Hop on a bike and explore the scenic Shining Sea Bikeway, relax on Old Silver Beach, or explore the shops and cafés in nearby Falmouth Village. For a romantic excursion, hop on the ferry to Martha's Vineyard or enjoy a sunset picnic by the shore.

350 Quaker Road, North Falmouth, MA 02556

4.0 Star Rating | Read Reviews

Canopy by Hilton Boston Downtown, Boston, Massachusetts

Photo: Canopy by Hilton Boston Downtown

Located in the vibrant heart of Boston's historic downtown, Canopy by Hilton Boston Downtown offers up a warm-weather urban retreat for those seeking a romantic getaway in Massachusetts for couples. The property overlooks the picturesque Rose Kennedy Greenway and is surrounded by old-timey cobblestone streets filled with charming cafés, boutique shops and the city's most iconic landmarks. While Boston is a great city to explore in the spring and summer months, we also love this hotel because it provides free bike rides for easy exploration around the bustling city.

Things to Do: Take a trolley tour of Boston, walk the historic Freedom Trail, explore Boston's donut scene, and eat, drink and shop at the bustling Faneuil Hall Marketplace

99 Blackstone Street, Boston, MA 02109

4.6 Star Rating | Read Reviews

Chatham Bars Inn, Chatham, Massachusetts

Photo: Chatham Bars Inn

For those who like their classic New England romance with a bit of a buzz, Chatham Bars Inn delivers. Less than two hours from Boston, it's the perfect quick hit of seaside magic. "Perched above a private stretch of beach—with Adirondack chairs just begging for sunset snuggles—it's equal parts elegance and energy," Poole says. In the summer, enjoy sparkling beach views from your coastal-cozy rooms, parktake in clam bakes and venture to the shoreline.

Things to Do: Soak up the sun on the private beach, take a scenic boat ride to North Beach Island, and enjoy a romantic dinner with sweeping ocean views at one of the inn's waterfront restaurants. Oh, and don't miss sunrise or sunset at Chatham Lighthouse!

297 Shore Road, Chatham, MA 02633

4.3 Star Rating | Read Reviews