From cozy historic inns in the Berkshires to charming bed and breakfasts on the islands to the luxe hotels of Boston, we have found some of the most romantic getaways in Massachusetts. Whether you are seeking a couple’s weekend getaway or a special spot to celebrate a special anniversary, birthday, or Valentine’s Day, you can find the perfect match for you and your significant other.
From the mountains to the beaches, we have searched for the most romantic, most unique destinations in Massachusetts for a romantic getaway with your special someone in all seasons. See other romantic getaways in the Northeast or New England.
Romantic Getaways on Cape Cod & The Islands
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1. Nobnocket Boutique Inn, Vineyard Haven, Martha’s Vineyard
The Nobnocket Boutique Inn is a seven-room property on Martha’s Vineyard, set on almost two acres of gardens and woodland to form a secluded island getaway. The Inn is a historic Arts & Crafts manor house with a very contemporary and upscale interior design. Open year-round, the inn features a large communal fireplace and fireplaces in several of the rooms to keep you cozy even in the chilly months.
The inn’s breakfast has won awards for years and in 2021, the Inn was awarded a Readers’ Choice Award by Conde Nast Traveler. Only those over 16 years of age are welcomed, creating a relaxing and romantic escape for adults looking to celebrate honeymoons, anniversaries, birthdays, or just that rare night away.
All rooms feature luxurious Frette linens and large bathrooms with tile and glass walk-in showers and stand-alone soaking tubs. The Inn offers daily, complimentary outdoor yoga for our guests throughout the summer and the concierge services can arrange experiences for couples such as private sailing trips, boat charters to secluded beaches, in-room massages, waterfront dining, alpaca yoga, private cheese tasting at the award-winning Grey Barn Farm, sunset kayaking trips, photoshoots, and complimentary bike use.
Check rates and reviews for the Nobnocket Boutique Inn
2. Chapter House, Yarmouth Port
Centrally located to Boston, Providence, and NYC, Cape Cod makes for the perfect romantic weekend getaway. Of course, it is lovely in the summer, but if you are looking for a quieter romantic getaway, plan to visit during the shoulder seasons. Opening in April 2022, the Chapter House is nestled into two acres in the Cape town of Yarmouth Port.
One of the largest Inns on Cape Cod, this historical property sits directly on Old King’s Highway/Route 6A in charming Yarmouth Port. Around Chapter House, guests can lounge on the lawn, walk the property and cute neighboring streets, or enjoy a specially crafted cocktail while watching a Cape sunset. Off property, guests will see the fun continues with amazing restaurants and gorgeous beaches, making for the most relaxing of weekend getaways.
The main house is three stories, with a beautifully updated bar, and a four-season porch. The Carriage House consists of 10 fully remodeled guest rooms all with private baths.
Check rates and reviews for the Chapter House
3. Wequassett Resort and Golf Club, Harwich
Open April through November, the Wequassett Resort and Golf Club offers suites and cottages that offer the perfect blend of luxury and seaside charm for those looking for a full resort experience, including pools, fine dining, and activities ranging from GLO paddleboarding to fitness classes.
With a separate adults-only pool, as well as a small beachfront and private boat shuttles to the Cape Cod National Seashore, the Wequassett makes a perfect warm-weather romantic retreat. However, many of the resort’s guest rooms and suites also offer cozy fireplaces if you are visiting in the chillier off-season.
Nearby, guests can enjoy shopping in the charming town of Chatham or watching the seals come to eat at the Chatham Fish Market. It is also easy to explore the rest of the Cape from whale watching and dunes tours in Provincetown to days enjoying the National Seashore or visiting some of the Cape’s famous lighthouses.
Check rates and reviews for the Wequassett Resort
4. AutoCamp Cape Cod, Falmouth
Looking for something unique, fun, and a little retro to spice things up? Try a weekend getaway to AutoCamp Cape Cod. These classic Airstream trailers are decorated with a modern design and everything you need for a comfortable glamping experience, from air conditioning to heat, to Bluetooth sound, and even WiFi. This is the perfect spot for a workcation or nature retreat.
Located right on the bike path that runs from Falmouth to Woods Hole, it is easy to get out and explore. On-site you can enjoy the restaurant and lounge or purchase kits to cook over your own fire. A romantic getaway to AutoCamp Cape Cod is perfect for couples looking for a quirky and Instagramable getaway.
For a limited time, you can save $20 off a stay at Auto Camp by using my referral link(and I’ll get a $20 credit towards my next stay too!)
See my full review of AutoCamp Cape Cod
5. Ocean Edge Resort, Brewster
Located along the coast of Massachusetts, Ocean Edge Resort & Golf Club has rightfully earned its spot as one of Cape Cod’s crown jewels. With luxurious accommodations, a plethora of resort activities, and close proximity to the vineyards and shops of Brewster, Ocean Edge Resort is the perfect spot for a romantic getaway.
Couples looking for fun and unique activities for two can explore all the resort has to offer including a couple’s massage at The Beach House Spa, a friendly game of golf on the Cape’s only Nicklaus Design course, a swim in one of their multiple heated pools, a scenic walk on the resort’s 700-foot stretch of private beach, and so much more. Couples can also spend quality time together enjoying different activities such as mixology lessons, trivia nights, and karaoke.
This year-round resort also rolls out consistent seasonal romantic offers, like private dining in a heated igloo for winter at The Frost Bar, so couples aren’t just limited to one season.
Check rates and reviews at the Ocean Edge Resort
6. Lighthouse Inn, West Dennis
Picturesquely situated on the shores of Nantucket Sound in West Dennis, the Lighthouse Inn is a romantic setting for a couple’s getaway and is a popular wedding venue as well. The Inn is anchored by an 1850s-era lighthouse still in operation today.
With 550 feet of private beach and directly adjacent to over 1.5 miles of public beach, Lighthouse Inn is the premier destination for long walks on the beach. The Inn offers oceanfront dining and fire pits for a romantic sunset dinner or après-beach cocktails. Complimentary recreational amenities include a tennis court, lawn games, a visiting ecologist, outdoor oceanfront movie nights, and a solar-heated pool. Oceanview cottages offer porches with Adirondack chairs and balance privacy with sweeping views of the gentle ebb and flow of the tide.
Nearby activities for two include numerous nature trails, the Cape Cod Rail Trail bike path to Eastham, 9 golf courses, couples’ parasailing, JetSki rentals, ferries to Nantucket and Martha’s Vineyard, and whale watching tours. The Inn has been owned and operated by the Stone family for over 84 years.
Check rates and review at the Lighthouse Inn
7. The Brass Lantern Inn, Nantucket
The Brass Lantern Inn is a perfect spot for a weekend in Nantucket. It is a short walk from the ferry port and is within easy walking distance to all the shops and restaurants. Guests can even walk to Steps Beach or rent a bike to explore the island.
The Inn offers seventeen guest-rooms with en-suite baths, and one and two-bedroom suites, which are perfect for small groups or families. There is a sitting room and library downstairs for relaxing and the Innkeepers provide your choice of breakfast items and freshly-baked cookies in the later afternoon.
Check rates and reviews at The Brass Lantern Inn
Boston Romantic Getaways
8. Boston Harbor Hotel, Boston
If you prefer a city break or staycation for a romantic getaway, my vote is for the Boston Harbor Hotel, Boston’s only Five Star waterfront hotel. Designed with couples in mind, the hotel offers a Romance Package, which includes a bottle of Moet Champagne and gourmet chocolate-dipped strawberries delivered to your room upon arrival.
Located in the heart of downtown Boston, romantics can enjoy the seaside views or charter a private boat right from Rowes Wharf for a picturesque romantic evening. Walking distance to shopping in Faneuil Hall, dining in the North End and the Seaport, Boston Harbor Hotel is located right near the action.
Check rates and reviews for the Boston Harbor Hotel
9. The Newbury, Boston
The Newbury Boston, which opened in May 2021 in one of the city’s most iconic landmark buildings, has been transformed into a 286-room luxury hotel. Adjacent to the Boston Public Garden, The Newbury has the best vantage point for viewing the Garden’s winter scenery. The Newbury and its iconic destination in the Back Bay, make for the most romantic stay to experience all that Boston has to offer from shopping the boutiques and galleries of Newbury Street to Copley Square, the 1800s landmark Trinity Church, the Boston Public Garden, and the Boston Public Library.
The hotel’s luxurious and picturesque fireplace suites are perfect to indulge in a cozy escape. From classic New England maple to fragrant cherry, guests can select the wood varietal perfect for the ambiance they wish to create. And, with the expert services of the hotel’s Fireplace Butler, guests can relax fireside in no time.
Downstairs, The Street Bar offers a cozy atmosphere featuring a roaring fireplace, with warming cocktails, while the hotel’s adjacent private library lounge, curated by the Boston Public Library, also offers hotel guests the experience to enjoy a book while lounging fireside.
From a snow-dusted stroll in the Public Garden to cozy fireside cocktails to dinner overlooking the twinkling city lights at Contessa, there are countless romantic moments to experience at The Newbury Boston. This Valentine’s Day, guests can enjoy a romantic weekend escape, by booking an elegant guest room or suite and receiving a welcome Champagne amenity, breakfast for two from Personal Dining, and a late check out of 3:00 p.m to savor every last moment.
Check rates and reviews at The Newbury
Romantic Getaways on the North Shore
10. Inn at Castle Hill, Ipswich
The Inn at Castle Hill is set on the 2,100 acres Crane Estate in Ipswich, MA, just north of Boston. I’ve attended a wedding on this conservation compound and it is just beautiful. The estate includes the Inn, the Great House at Castle Hill (a National Historic Landmark), and the renowned Crane Beach and Wildlife Refuge.
Guests can enjoy walking the grounds of the beautiful property with a self-guided tour using the TourTrustees app, participate in a Full Moon Hike, Snowy Owl Prowl, and enjoy the beautiful north shore including nearby Appleton Farms.
The cozy living room has a lovely fireplace and guests can order wine, beer, and cheese platters to enjoy, making a cozy romantic getaway.
Check rates and reviews for the Inn at Castle Hill
11. Harbor Light Inn, Marblehead
Samantha from New England Wanderlust recommends the Harbor Light Inn in Marblehead. This quintessential, cozy inn has 20 beautiful rooms that showcase stunning 18th-century design elements but also provide luxurious and modern amenities. Harbor Light perfectly balances history with modern coziness like soft sheets and blankets.
Each room is individually decorated for a unique experience – some even with fireplaces and jetted tubs for two. The inn has an on-site tavern serving food and drinks, and also provides a gourmet breakfast each morning, included with your stay. You can even request to have your breakfast delivered to your room to elevate your romantic getaway. In-room couples massages will also gladly be arranged for you by the inn’s friendly and welcoming staff.
The town of Marblehead is a true sailing and maritime community on the water, and Harbor Light is perfectly situated in the heart of the historic village, making it effortless to walk to the water, restaurants, and locally owned boutiques and cafes for a day of casual strolling. The inn also has an outdoor pool that can be used during the warmer months and provides on-site parking, which is extremely valuable for a small, historic town.
Check rates and reviews at Harbor Light Inn
12. Briar Barn Inn, Rowley
Located just a few minutes from Crane Beach and a short 15-minute drive to charming Newburyport, the Briar Barn Inn is a popular spot for weddings, rehearsal dinners, and romantic getaways. I was recently hosted by the Briar Barn Inn and enjoyed staying in a spacious one-bedroom suite with our own fireplace and very large bathroom with a shower and a separate soaking tub.
Briar Barn Inn is full of special touches like freshly-baked cookies in the afternoon, hot apple cider in the lobby, coffee bars throughout the inn, cozy seating areas, indoor and outdoor fireplaces, and a fresh pastry cart for breakfast. When staying at the Briar Barn Inn, you don’t need to leave. The Grove restaurant offers delicious regional fare in a beautiful barn-like setting. Relax and enjoy a massage, facial, or foot soak at the Spa on property.
Check rates and reviews for the Briar Barn Inn
Romantic Getaways on the South Shore
13. Mirbeau Inn & Spa, Plymouth
Located between Boston and Cape Cod, Plymouth offers ocean views in a town steeped in history. In the summer, you can take a whale watch or paddlewheel boat harbor cruise, visit Plimoth and Pawtuxet Museums, or the Mayflower II.
The Mirbeau Inn & Spa offers the perfect accommodations for a romantic weekend getaway in Plymouth. Nestled in The Pinehills of Plymouth, the French Chateau-style Mirbeau offers miles of walking paths that meander through the woods and a variety of shops in its own little village.
There are 16 guest rooms located in the Manor House, including two romantic Turret Suites and two elegant one-bedroom Suites. All hotel guest rooms feature a warm and inviting fireplace, oversized bathrooms equipped with walk-in showers, soaking tubs, double sinks, and gorgeous views of the Monet pond garden or the Village Green of The Pinehills Community in Plymouth, MA.
Check rates and review for the Mirbeau Inn & Spa
Romantic Getaways in The Berkshires
14. The Cornell Inn, Lenox
The Cornell Inn, in Lenox, was originally three standalone buildings built between 1777 and 1888. In June of 2021, the new owner, Kurt Inderbitzin, reimagined and completely renovated The Cornell Inn. Featuring the works of 23 BIPOC designers, the 28-guest rooms in the Main House and nearby Carriage and Kerouac houses, along with the public spaces, have completely transformed this historic bed and breakfast.
Today, the Inn offers inviting designer rooms; a gourmet, table-served breakfast; a spectacular tavern; unbelievably delicious coffees, lattes, cappuccinos, and espressos; and, depending on the season, fresh home-made ice cream, or warm cider with cinnamon; and, in the evenings, cognac. All rooms come with their own walk-in showers, Keurig machines, cable TV, and private bathrooms and many of the rooms have a fireplace and private balconies.
Ideal for Valentine’s Day and romantic escapes throughout the colder months, each of the newly renovated guest rooms come with a bottle of champagne, and 17 of the rooms have private fireplaces with complimentary wood provided by the Inn for couples to cozy up to during their romantic getaway.
Check rates and review for The Cornell Inn
15. Porches Inn at Mass MoCA, North Adams
Skiers and art lovers will find an ideal romantic winter getaway at the Porches Inn at MASS MoCA, steps away from the largest contemporary art museums in the country and a short drive from one of the Berkshires’ favorite ski resorts, Jiminy Peak Ski Resort.
Porches Inn incorporates seven renovated Victorian-era buildings. The Inn’s 26 distinctive guest rooms and 18 suites employ a clever synthesis of retro and contemporary designs. The Inn offers a year-round outdoor heated pool, hot tub, sauna, bonfire pit, and fitness room.
Check rates and reviews for The Porches Inn
16. Seven Hills Inn, Lenox
Seven Hills Inn, set on 27 acres of lush lawns and stunning gardens, is a historic mansion comprised of 56 stylishly renovated guest rooms and suites located in three separate buildings, each with its own distinctive style: Manor House, Carriage House, and Terrace House.
The majority of the rooms in the Manor House overlook the inn’s lawns and stunning gardens. The spacious guest rooms in the Carriage House each feature a kitchenette for those that prefer to be more self-sufficient. Each of the spacious, light-filled rooms of the Terrace House faces the magnificent tree-lined grounds. This historic inn offers all the modern comforts including Bluetooth radios and USB plugs, 49- inch televisions, telephones, and complimentary wi-fi for the contemporary couple.
This estate offers ultimate privacy while boasting a culturally-rich locale, located in Lenox, just minutes away from attractions such as Tanglewood (summer home of the Boston Symphony Orchestra), Jacob’s Pillow Dance Theatre, Edith Wharton’s estate, The Mount, right next door, and Shakespeare & Company in the heart of the Berkshires.
Check rates and reviews for the Seven Hills Inn
Other Romantic Getaways in Massachusetts
17. Inn at Hastings Park, Lexington
The Inn at Hastings Park in historic Lexington, MA, is ideal for romantic getaways in all seasons. The Boston area’s only Relais & Châteaux property, the Inn features 22 stylishly luxurious accommodations that span three restored historic buildings and merge Lexington’s historic heritage and architecture with a contemporary American chic design. Each guest room has its own unique decor and incredibly comfortable beds. Some rooms also include antique-restored tile fireplaces, bathtubs, couples’ sinks, and rain showers.
An immersive food and wine destination unlike any other in New England, the Inn provides a seasonal menu at upscale Town Meeting Bistro, to the exclusive Culinary Garden and Inn owner and culinary educator Trisha Pérez Kennealy also shares her passion for teaching in her role as Culinary Educator, offering indoor and outdoor cooking classes for hotel and day guests alike.
To up the romance ante all year round, the Culinary Garden featuring Whispering Angel (spring/summer months) and INNgloo Wonderland (winter months) offers an intimate dining experience for lunch, dinner, or weekend brunch.
Many Revolutionary War landmarks are within steps of the Inn at Hastings Park. Guests can walk the path that Paul Revere and William Dawes followed on their Midnight Ride to the nearby house where John Hancock and Sam Adams bunked down. The Battle Green, where the Shot Heard Round the World started the first battle of the Revolution, is a short walk from The Inn. Just further down the road, The Munroe Tavern, which the British Redcoats took over on their retreat back to Boston—and where George Washington once dined—is worth a visit. The Liberty Ride® also includes a trolley tour of the many historic sites in the area, such as famous taverns and battlefields.
The Inn is also situated along the Minuteman Bikeway, a beloved 11-mile rail trail, and they have their own fleet of bikes and helmets available for use. Other nearby recreational activities include hiking, cycling, cross-country skiing, and canoeing, depending on the season. Additionally, Lexington’s proximity to Concord allows those interested in American literature to visit the homes of famous authors near our hotel, including Ralph Waldo Emerson, Louisa May Alcott, and Nathaniel Hawthorne, as well as tour Walden Pond, where transcendentalist Henry David Thoreau lived and wrote.
Check rates and reviews for the Inn at Hastings Park
Looking for more ideas?
Check out these related articles:
- Romantic getaways in Vermont
- Romantic getaways in New Hampshire
- Romantic getaways in Rhode Island
- Romantic getaways in Connecticut
- Most romantic resorts in the USA
Feature image courtesy of Ocean Edge Resort.
Tamara is an over 50, award-winning travel writer, and recent empty nester based in Rhode Island. After years of writing about family travel on We3Travel and inspiring wanderlust as co-host of the Vacation Mavens family travel podcast, she started Your Time to Fly as a place to share ideas for girlfriend getaways, romantic escapes, and solo female travel for midlife women.
