Eastern Massachusetts Romantic Vacations 2026

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Top Romantic vacation packages in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

Eurostars The Boxer

West End

￥103,802

per person

Oct 18 - Oct 20

found 1 day ago

Roundtrip flight included

New York (LGA) to Boston (BOS)

8.8/10 Excellent! (1,588 reviews)

Boston Harbor Hotel

North End

Save 100% on your flight

￥168,418

per person

Oct 18 - Oct 20

found 1 day ago

Roundtrip flight included

New York (LGA) to Boston (BOS)

9.8/10 Exceptional! (1,014 reviews)

Fairmont Copley Plaza, Boston

Back Bay

Save 100% on your flight

￥122,536

per person

Oct 18 - Oct 20

found 1 day ago

Roundtrip flight included

New York (LGA) to Boston (BOS)

9/10 Wonderful! (1,317 reviews)

Everything was perfect!

Reviewed on Sep 18, 2026

Hotel AKA Back Bay

Back Bay

￥114,506

per person

Oct 18 - Oct 20

found 1 day ago

Roundtrip flight included

New York (LGA) to Boston (BOS)

9.4/10 Exceptional! (1,338 reviews)

The Lenox Hotel Boston

Back Bay

￥113,893

per person

Oct 18 - Oct 20

found 1 day ago

Roundtrip flight included

New York (LGA) to Boston (BOS)

9.6/10 Exceptional! (1,699 reviews)

Very friendly staff and ready to help at all times. Perfect location.

Reviewed on Sep 17, 2026

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5* Romantic vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

Boston Harbor Hotel

North End

Save 100% on your flight

￥168,418

per person

Oct 18 - Oct 20

found 1 day ago

Roundtrip flight included

New York (LGA) to Boston (BOS)

9.8/10 Exceptional! (1,014 reviews)

The Langham, Boston

Downtown Boston

￥396,536

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Tokyo (NRT) to Boston (BOS)

9.8/10 Exceptional! (1,007 reviews)

InterContinental Boston by IHG

Downtown Boston

￥319,886

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Tokyo (NRT) to Boston (BOS)

9.4/10 Exceptional! (1,166 reviews)

Don't see what you're looking for?

See all available trips from New York to Eastern Massachusetts

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4 Night Romantic vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

Eurostars The Boxer

West End

￥270,878

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Tokyo (NRT) to Boston (BOS)

8.8/10 Excellent! (1,588 reviews)

Boston Harbor Hotel

North End

￥338,134

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Tokyo (NRT) to Boston (BOS)

9.8/10 Exceptional! (1,014 reviews)

The Langham, Boston

Downtown Boston

￥396,536

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Tokyo (NRT) to Boston (BOS)

9.8/10 Exceptional! (1,007 reviews)

Don't see what you're looking for?

See all available trips from Tokyo to Eastern Massachusetts

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Top Romantic Eastern Massachusetts Hotels

Seaport Hotel Boston

1 Seaport Lane Boston MA

6 min walk from Fenway Park

A garden, a lobby fireplace, and premium mattresses await couples visiting this romantic hotel. The property also offers onsite dining, a bar, and a waterfront ...

9.6/10 Exceptional! (4,994 reviews)

Couples like: onsite spa services, bar

Travelers say...

"Excellent!"

Reviewed on Sep 18, 2026

Nantasket Beach Resort

45 Hull Shore Drive Hull MA

13 min drive from Fenway Park

A hot tub and in-room fireplaces await at this romantic hotel, which also offers premium mattresses and a beachfront location.

Hotel AKA Boston Common

90 Tremont St Boston MA

15 min walk from Fenway Park

You and your sweetheart are sure to love the premium mattresses and luxury bedding at this boutique hotel. You'll also appreciate the restaurant, bar, and local ...

See all 16,243 properties in Eastern Massachusetts

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.