Massachusetts

10 Chill Romantic Getaways in Massachusetts

by Dustin Christensen
Updated August 08, 2022

romantic getaways in massachusetts
Photo: Airbnb

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From the scenic coastlines of the Cape to the panoramic hills of the Berkshires, Massachusetts’ romantic landscapes don’t disappoint.

The diversity of Massachusetts’ lands makes for an interesting mix of couples’ vacations, so whether you need a lively weekend in Beacon Hill, a mellow island trip, or time to unwind in the woods, The Bay State has you covered.

Here are 10 of the best romantic getaways to book in Massachusetts the next time you need a charming couple’s retreat.

1. Waterfront Bungalow

romantic bungalow massachusetts
Photo: VRBO

Why you should stay: serene oceanfront cottage for two.

  • Location: North Truro
  • Sleeps: 2
  • Minimum stay: 3 nights
  • Rates start from: $275/night

It doesn’t get much more romantic than watching sunsets on the Cape, and this one-bedroom cottage near Provincetown proves it. The home is well-stocked, immaculately clean and not far from shops and restaurants — check out Fanizzi’s Restaurant by the Sea for a romantic dinner on the water.

For day trips in the area, visit Truro Vineyards, an award-winning family-owned winery offering daily tastings and tours — and a wine club for folks who wanna keep the vibe goin’ year-round.

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Related Read: 7 Spectacular Weekend Road Trips from Boston, Massachusetts

2. The Nantucket Hotel & Resort

The Nantucket Hotel & Resort
Photo: Shutterstock

Why you should stay: throwback luxury digs near the island’s best sights.

  • Location: Nantucket
  • Sleeps: 2+
  • Minimum stay: 1 night
  • Rates start from: $225/night

Nantucket’s only year-round hotel is also its most iconic — you’ll catch its signature antique fire truck and bus transporting guests all around the island. The Nantucket Hotel & Resort first opened in 1891 as the Point Breeze, and a renovation began in 2012 quickly made it one of the most romantic hotels in New England.

Today, more than 40 accommodations — hotel rooms, suites and cottages — are available at the lux hotel, which serves delectable coastal dishes from its restaurant, Breeze. The Nantucket Club offers daily activities in any season, and you can purchase extras — think champagne, roses, chocolate-covered strawberries — to elevate your romantic stay.

Two heated pools, personal training and massage services all make for an unforgettable getaway, and if you visit in the offseason, you’ll have an even more intimate stay without the swarming summer crowds.

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3. Glass Treehouse

romantic treehouse MA
Photo: Airbnb

Why you should stay: cozy modern cabin in the woods.

  • Location: Otis
  • Sleeps: 4
  • Minimum stay: 2 nights
  • Rates start from: $350/night

This unique treehouse-esque home sits on 7 acres of forested land, so it’s quiet, dark and perfect for warm nights around the modern fireplace. Massive wall-sized windows open to expansive views of the area, offering romantic views — especially in the fall and winter.

“We were able to book an extra night after we found out how incredible it was and the communication was great,” said one Airbnb guest. “This is one of the most romantic places either of us have been.”

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Related Read: 10 Best Airbnb Rentals in Massachusetts

4. XV Beacon

XV Beacon hotel MA
Photo: XV Beacon

Why you should stay: award-winning amenities in a heritage-style hotel with deep Boston roots.

  • Location: Boston
  • Sleeps: 2+
  • Minimum stay: 1 night
  • Rates start from: $420/night

XV Beacon — pronounced “Fifteen Beacon” for its address — is an intimate hotel near Boston Common and the Massachusetts State House. Where most hotels in the area feel busy, stays at XV Beacon feel private and “residential,” in their words, and guests tend to agree.

There are only 7 rooms to each level, and 7 types of suites range from 300 square feet to a sprawling 1,400-square-foot, 2-bedroom suite with any amenity you can dream of. Each room contains a fireplace and exquisitely designed décor for a romantic stay you and your partner won’t forget.

For an even more personal touch, consider the hotel’s “Romance on the Hill” package, or in-room dining from Mooo…., the hotel’s signature steakhouse. It’ll completely redefine your idea of staying in for the night.

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5. Windmill Cottage

Windmill Cottage MA
Photo: VRBO

Why you should stay: maritime-influenced rental on the southern tip of Cape Cod.

  • Location: Chatham
  • Sleeps: 4
  • Minimum stay: 3 nights
  • Rates start from: $270/night

The Windmill Cottage is near some of Chatham’s most historic buildings, including the Chatham Lighthouse and a restored 1797-era windmill built by Col. Benjamin Godfrey. The home retains the historic neighborhood’s charms and character, from the post-and-beam style design to the retro appliances throughout the small home.

A beautifully manicured landscape complements the cottage’s quaint coziness, and its within walking distance of shops, dining and beaches. An outdoor shower makes it easy to clean up after a day on the cape before heading out for fresh seafood at nearby spots like Captain’s Table.

“It is hard to overstate how wonderful this place was to stay,” said one VRBO guest. “The location could not be more perfect from sunrise to sunset.”

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Related Read: 10 Terrific Tiny House Rentals in Massachusetts

6. Eliza Cottage

romantic cottage ma
Photo: VRBO

Why you should stay: quintessential island stay in a gorgeous central location.

  • Location: Nantucket
  • Sleeps: 4
  • Minimum stay: 1+ nights
  • Rates start from: $330/night

Nantucket’s resorts are world-class, but so are their vacation rentals, including Eliza Cottage, an impeccably decorated cottage overlooking the harbor near Children’s Beach. It’s the perfect place to spend a low-key week exploring downtown, nearby Brant Point Lighthouse and the area’s best eats, like The Proprietors bar & table and The Beet.

Eliza Cottage is stocked with premium appliances, comfortably efficient living spaces and a Stearns & Foster bed that’s hard to leave in the morning, especially if you’re visiting in cooler off-season months. Look through the cottage’s VRBO reviews and you’ll find a ton of repeat guests, so you may need to book far in advance to compete with the home’s growing fanbase.

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7. Berkshires Tower

silo tower cottage
Photo: Airbnb

Why you should stay: fancifully intimate weekend in the Berkshires.

  • Location: Lee
  • Sleeps: 2
  • Minimum stay: 2 nights
  • Rates start from: $290/night

Santarella Gardens is home to Massachusetts sculptor Henry Hudson Kitson’s former estate, a beautiful 4-acre property with lush gardens, winding trails and a fairy-tale-like silo and home.

The tower is an idyllic two-person getaway in the Berkshires, where just the right amount of space offers a whimsical stay reminiscent of the Massachusetts Renaissance Faire just north in Cummington. The upstairs bedroom is the home’s highlight, where a canopied bed and open windows look like they came from a Disney movie.

“The grounds were stunning,” said Airbnb guest Lisa. “A very dreamy romantic place.”

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Related Read: 15 Best Hiking Trails Near Boston, Massachusetts

8. The Merchant Salem

The Merchant Salem
Photo: The Merchant Salem

Why you should stay: former merchant’s home turned lux boutique hotel.

  • Location: Salem
  • Sleeps: 2+
  • Minimum stay: 1 night
  • Rates start from: $299/night

In 1789 — his first year in office — George Washington stayed at the Joshua Ward house, the building that is now The Merchant Salem. Today, guests can stay in a renovated version of the very room the Sage of Mount Vernon slept, or in a handful of other 300-square-foot suites that offer space to cozy up in a historic setting.

joshua ward house
Joshua Ward House. Photo: Wikimedia Commons

The Merchant’s storied past is part of the hotel’s allure, and its central location makes it easy to walk to Salem’s attractions, like the House of the Seven Gables and the Peabody Essex Museum. The land here once belonged to George Corwin, the sheriff who resided over the Salem witch trials, so if your idea of romance includes ghosts, hit up The Merchant next time you’re in town.

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9. Rustic Farm Cabin

romantic farm cabin ma
Photo: Brian & Natasha, Hipcamp

Why you should stay: simple cabin getaway on bucolic Berkshires farmland.

  • Location: Sheffield
  • Sleeps: 2
  • Minimum stay: 2 nights
  • Rates start from: $78/night

Couples looking for less polish and more Thoreau-style solitude will dig the rustic cabin at Moon in the Pond Farm in the Berkshires. There’s no WiFi or heat beyond the cabin’s aged woodstove, so it’s a minimalist stay with quiet nights and a focus on the farm’s beautiful landscape.

“An absolutely idyllic stay,” said Hipcamper Sarah G. “The cabin was so comfortable and private.”

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Related Read: 8 Best Beach Camping Spots in New England for an Oceanfront Getaway

10. Tramonto Sul-Lago

Tramonto Sul-Lago
Photo: Airbnb

Why you should stay: tranquil lake views in a fully renovated waterfront home.

  • Location: Wales
  • Sleeps: 6
  • Minimum stay: 2 nights
  • Rates start from: $299/night

Gorgeous wood beams and a refined interior frame views of Lake George from this lake cottage in southern Massachusetts. Outside, you’ll find a relaxing deck overlooking the lake, and a dock, outdoor shower and kayaks make it easy to fully embrace the outdoors here.

Clean lines, open spaces and natural light create a cozy ambiance to the cottage, whose name means “sunset over lake.” Need we say more?

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