Western Massachusetts Romantic Holidays

Book a Romantic Hotel + Flight or Car together to unlock savings

Photo by Photo courtesy of Berkshire Visitors Bureau
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How to find a romantic Western Massachusetts holiday

How can I find the best Western Massachusetts vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Western Massachusetts. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Western Massachusetts romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Western Massachusetts that start from . Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Western Massachusetts romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Western Massachusetts?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Western Massachusetts?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Western Massachusetts that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Western Massachusetts with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Western Massachusetts romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.

Top Romantic Western Massachusetts Hotels

D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
  • 39 min drive from Six Flags New England
Stay at this 3-star spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants and room service. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (2,282 reviews)

Couples like: full-service spa, couples spa treatments, bar, Hot tub

Travellers say...
"Room was clean and staff was wonderful, only issue was loose toilet seat, and you needed to hold the handle down to flush toilet"

Reviewed on 2 Jul 2025

D. Hotel Suites & Spa
Shaker Mill Inn
Shaker Mill Inn
2.5 out of 5
2 Oak Street, West Stockbridge, MA
  • 54 min drive from Six Flags New England
Stay at this property in West Stockbridge. Enjoy free breakfast, free parking and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer ...
9.6/10 Exceptional! (385 reviews)
"Very cute and clean room. After driving all day we were so happy to see all muffins, scones, yogurt, cereal, oatmeal, strawberries, milk, OJ, hot chocolate and coffee already in the room for breakfast the next day. We had a great stay, thank you!"

Reviewed on 2 Jul 2025

Shaker Mill Inn
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 1 hour drive from Six Flags New England
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,847 reviews)
"amazing for the price and overall SOOO clean"

Reviewed on 28 Jun 2025

Vacation Village in the Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.