Eastern Massachusetts Romantic Holidays

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

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    Packages with flights are ATOL protected

Top flight + Romantic hotel deals in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.
Hotel AKA Boston Common

Hotel AKA Boston Common

Downtown Boston
£3,229
per person
21 Sept - 24 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (1,732 reviews)
Great staff, Saheed was pleasant and courteous. Lovely room, clean and nice modern furniture. The staff in the restaurant are very attentive and friendly, the bartender Kathleen made excellent mixed drinks and was pleasant to talk to.

Reviewed on 14 Aug 2026

Hotel AKA Back Bay

Hotel AKA Back Bay

Back Bay
£3,336
per person
21 Sept - 24 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (1,272 reviews)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
£3,580
per person
21 Sept - 24 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (1,298 reviews)
Revere Hotel Boston Common

Revere Hotel Boston Common

Bay Village
£3,338
per person
21 Sept - 24 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,112 reviews)
The hotel was in a good location. Our room a suite was a good size . Sadly the bathroom let it down with an obvious repair to the tiled shower floor with an excessive amount of rough grouting over the tiles and drain.Which you could feel when standing in shower! The white grouting in the shower was beginning to look yellow. There was something splattered on the wall as small dark splashes were evident. The door to the bathroom had marks and smears on it. There was a white plastic fractured waste bin no lining in corner. The drawer unit in bedroom had a lacquer finish to it and had marks and smears on it Generally the room looked like it needed updating. Unfortunately noise travelled through a connecting door from other guests !

Reviewed on 15 Aug 2026

The Newbury Boston

The Newbury Boston

Back Bay
£3,809
per person
21 Sept - 24 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (702 reviews)
The Newbury is fabulously located across the street from the Public Garden and steps away from the amazing shopping area of Newbury St. Our room was clean and comfortable. The staff was very nice and helpful.

Reviewed on 13 Aug 2026

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5* Romantic holidays in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston

The Langham, Boston

Downtown Boston
£1,222
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
I’ve stayed at the Langham before and have never been disappointed! The staff is incredible, housekeeping is superb and the property itself is just beautiful!

Reviewed on 13 Aug 2026

The Newbury Boston

The Newbury Boston

Back Bay
£3,809
per person
21 Sept - 24 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (702 reviews)
The Newbury is fabulously located across the street from the Public Garden and steps away from the amazing shopping area of Newbury St. Our room was clean and comfortable. The staff was very nice and helpful.

Reviewed on 13 Aug 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
£1,924
per person
16 Oct - 21 Oct
found 7 hours ago
Return direct flight included
London (LON) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
Don't see what you're looking for?
See all available trips from London to Eastern Massachusetts
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3 Night Romantic holidays in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.
Hotel AKA Boston Common

Hotel AKA Boston Common

Downtown Boston
£3,229
per person
21 Sept - 24 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (1,732 reviews)
Great staff, Saheed was pleasant and courteous. Lovely room, clean and nice modern furniture. The staff in the restaurant are very attentive and friendly, the bartender Kathleen made excellent mixed drinks and was pleasant to talk to.

Reviewed on 14 Aug 2026

Hotel AKA Back Bay

Hotel AKA Back Bay

Back Bay
£3,336
per person
21 Sept - 24 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (1,272 reviews)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
£3,580
per person
21 Sept - 24 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (1,298 reviews)
Don't see what you're looking for?
See all available trips from Dublin to Eastern Massachusetts
View all trips

4 Night Romantic holidays in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston

The Langham, Boston

Downtown Boston
£1,363
per person
29 Oct - 2 Nov
found 14 hours ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
I’ve stayed at the Langham before and have never been disappointed! The staff is incredible, housekeeping is superb and the property itself is just beautiful!

Reviewed on 13 Aug 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
£1,888
per person
17 Oct - 21 Oct
found 17 hours ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
The Eliot Hotel

The Eliot Hotel

Back Bay
£2,235
per person
2 Nov - 6 Nov
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Don't see what you're looking for?
See all available trips from Glasgow to Eastern Massachusetts
View all trips

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 £1,222. 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.

Top Romantic Eastern Massachusetts Hotels

Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
  • 6 min walk from Fenway Park
Stay at this business-friendly hotel in Boston. Enjoy free Wi-Fi, 2 restaurants and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
9.6/10 Exceptional! (4,765 reviews)

Couples like: on-site spa services, bar

Travelers say...
"Great hotel! Lobby and restaurant are awesome. There is an entire gym for guests which I’ve never seen before. Location is great - safe and clean area with extremely close access to the bus that can take you to and from the airport. Also extremely quiet at night - got a good nights rest when I needed ..."

Reviewed on 15 Aug 2026

Seaport Hotel Boston
Nantasket Beach Resort

Nantasket Beach Resort

45 Hull Shore Drive Hull MA
  • 13 min drive from Fenway Park
Stay at this beach hotel in Hull. Enjoy free Wi-Fi, a beach locale and room service. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8.6/10 Excellent! (1,000 reviews)

Couples like: Hot tub, on the beach, fireplace

Travelers say...
"Clean Room"

Reviewed on 13 Aug 2026

Nantasket Beach Resort
Hotel AKA Boston Common

Hotel AKA Boston Common

90 Tremont St Boston MA
  • 15 min walk from Fenway Park
Stay at this boutique hotel in Boston. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,760 reviews)
"Great staff, Saheed was pleasant and courteous. Lovely room, clean and nice modern furniture. The staff in the restaurant are very attentive and friendly, the bartender Kathleen made excellent mixed drinks and was pleasant to talk to."

Reviewed on 14 Aug 2026

Hotel AKA Boston Common
See all 16,357 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.

Things to do

Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

£13
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

£38
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

£13
per traveller
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
See all activities in Eastern Massachusetts

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.