Eastern Massachusetts Romantic Vacations

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Flight and Romantic hotel deals in Eastern Massachusetts

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

Eurostars The Boxer

West End
CA $1,129
per person
Oct 31 - Nov 2
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8.8/10 Excellent! (1,597 reviews)
The hotel overall was ok. I would expect more from a 4 star hotel. Our room never seemed to be super clean. The carpets didn’t appear to get vacuumed and trash was left on the nightstand. We also got plenty of towels the first couple of nights but nights 3 and 4, they were scarce and I had to ask the front desk for some. That being said, the location was really good and concierge was nice and attentive but would probably look to stay somewhere else nearby next time.

Reviewed on Sep 30, 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
CA $1,313
per person
Dec 1 - Dec 3
found 4 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
The Langham, Boston

The Langham, Boston

Downtown Boston
CA $1,236
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
CA $1,134
per person
Oct 31 - Nov 2
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9/10 Wonderful! (1,345 reviews)
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

Back Bay
CA $1,157
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.2/10 Wonderful! (2,493 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Eastern Massachusetts
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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
CA $1,236
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

North End
CA $1,313
per person
Dec 1 - Dec 3
found 4 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
The Newbury Boston

The Newbury Boston

Back Bay
CA $2,042
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (732 reviews)
Don't see what you're looking for?
See all available trips from Columbus 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.
The Langham, Boston

The Langham, Boston

Downtown Boston
CA $1,236
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
CA $1,382
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
The Newbury Boston

The Newbury Boston

Back Bay
CA $1,660
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.4/10 Exceptional! (732 reviews)
Don't see what you're looking for?
See all available trips from Columbus 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 Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

Back Bay
Save 100% on your flight
CA $1,278
per person
Nov 8 - Nov 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (2,493 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
CA $1,501
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
The Langham, Boston

The Langham, Boston

Downtown Boston
Save 100% on your flight
CA $2,084
per person
Nov 8 - Nov 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Eastern Massachusetts
View all trips

Plan unforgettable romantic Eastern Massachusetts vacations

What are some of the benefits of booking a romantic Eastern Massachusetts vacation?

When booking a romantic Eastern Massachusetts vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in United States of America.

How can I find the best vacation packages for couples?

If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Eastern Massachusetts destination, and you'll be met with an array of options for you and your partner to enjoy.

Can I find cheap romantic vacations for 2 in Eastern Massachusetts?

Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $1,129 and can enjoy savings of up to 18 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first.

What do I need to consider when booking a romantic getaway in Eastern Massachusetts?

Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Eastern Massachusetts certainly come in handy here.

What amenities should I look for in a luxury romantic vacation?

If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Eastern Massachusetts.

Can I book a romantic Eastern Massachusetts vacation with a hot tub?

Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them.

How can I find romantic vacation getaways that are all-inclusive?

An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Eastern Massachusetts search.

Can I book a romantic trip to Eastern Massachusetts that is fully refundable?

Several romantic Eastern Massachusetts vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements.

Why should I book a romantic vacation with Expedia?

Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage.

Romantic Hotels in Eastern Massachusetts

Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
  • 6 min walk from Fenway Park
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
Seaport Hotel Boston
Nantasket Beach Resort

Nantasket Beach Resort

45 Hull Shore Drive Hull MA
  • 13 min drive from Fenway Park
Book a stay at this beach hotel in Hull. Enjoy free WiFi, a beach locale, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (1,013 reviews)
"Learned “Ocean View” does not mean facing ocean. It means you can see the ocean from somewhere in your room. Learned the Expedia price contracted is not the price you get because hotel staff say they can’t see it. Learned there is no manager on site to rectify issues like that. Staff had to try to ..."

Reviewed on Sep 29, 2026

Nantasket Beach Resort
Hotel AKA Boston Common

Hotel AKA Boston Common

90 Tremont St Boston MA
  • 15 min walk from Fenway Park
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
9/10 Wonderful! (1,808 reviews)
"Great location for walking tours of Boston; very friendly and helpful staff."

Reviewed on Sep 30, 2026

Hotel AKA Boston Common
See all 16,077 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.