A historic church with a large central tower and multiple spires, surrounded by modern buildings and a public square with people and greenery.

Eastern Massachusetts Romantic Holidays

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Top Romantic holiday packages in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.
  • 9 Oct - 14 Oct

    Revere Hotel Boston Common + Flight

    Bay Village
    5 nights
    4.0 star property
    9.0/10 - Wonderful (2,102 reviews)
    "It was pretty chill I guess"
    Reviewed August 3, 2026
    Return Dublin (DUB) - Boston (BOS)
    DUB - BOSDirect BOS - DUBDirect
    €1,807
    €1,429
    per traveller
    found 13 hours ago
    Revere Hotel Boston Common
  • 3 Oct - 8 Oct

    Boston Harbor Hotel + Flight

    North End
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,005 reviews)
    "We had a wonderful stay at the Boston Harbor Hotel. From the moment we booked, Demetri went above and beyond by helping us secure one of the best harbor view rooms, and it truly made our weekend special. Waking up to the waterfront views was unforgettable. The room was spotless, beautifully maintained, and extremely comfortable. Every staff member we encountered was friendly, professional, and genuinely eager to make our stay memorable. The hotel bar was excellent, with great cocktails and a..."
    Reviewed August 2, 2026
    Return Dublin (DUB) - Boston (BOS)
    DUB - BOSDirect BOS - DUBDirect
    €3,664
    €2,327
    per traveller
    found 1 day ago
    Boston Harbor Hotel
  • 23 Oct - 29 Oct

    The Lenox Hotel Boston + Flight

    Back Bay
    6 nights
    4.5 star property
    9.6/10 - Exceptional (1,642 reviews)
    "Bat"
    Reviewed August 2, 2026
    Return Dublin (DUB) - Boston (BOS)
    DUB - BOS1 stop BOS - DUBDirect
    €2,382
    €1,735
    per traveller
    found 14 hours ago
    The Lenox Hotel Boston
  • 19 Oct - 25 Oct

    Wyndham Boston Beacon Hill + Flight

    West End
    6 nights
    3.5 star property
    7.8/10 - Good (2,176 reviews)
    "The outdoor pool deck was so bad you could not walk on it barefoot. The pool bathrooms were so dirty it was unreal on a nice day. The gym is tiny and dirty. Hotel needs updating everywhere old and out of style as well as dirty"
    Reviewed August 2, 2026
    Return Dublin (DUB) - Boston (BOS)
    DUB - BOSDirect BOS - DUBDirect
    €1,943
    €1,491
    per traveller
    found 10 hours ago
    Wyndham Boston Beacon Hill
  • 3 Oct - 8 Oct

    Hotel AKA Back Bay + Flight

    Back Bay
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,293 reviews)
    "Clean and modern room. Spacious bedroom and bathroom, comfortable bed. Great location, walkable to many Boston attractions and close to public transport."
    Reviewed August 3, 2026
    Return Dublin (DUB) - Boston (BOS)
    DUB - BOSDirect BOS - DUBDirect
    €1,951
    €1,544
    per traveller
    found 1 day ago
    Hotel AKA Back Bay

Discover the most popular places to visit in Eastern Massachusetts

What to do in Eastern Massachusetts

Top Romantic Eastern Massachusetts Hotels

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.

How to find a romantic Eastern Massachusetts holiday

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

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Eastern 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 Eastern 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 Eastern Massachusetts that start from €1,429. Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Eastern 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 Eastern 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 Eastern 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 Eastern 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 Eastern 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 Eastern 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.