Massachusetts Romantic Vacations
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Top Romantic vacation packages in Massachusetts
Price found within the past 48 hours. Click for updated prices.
Crowne Pointe Historic Inn & Spa - Adults Only
Save 100% on your flight
Price was $790, price is now $514 per person
$514
per person
Jun 27 - Jun 29
found 15 hours ago
Roundtrip flight included
New York (NYC) to Provincetown (PVC)
9.2/10 Wonderful! (869 reviews)
Really cute and cozy vibe. Great location
Reviewed on Apr 19, 2026
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $1,293, price is now $800 per person
$800
per person
Jul 26 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Wilmington (ILG) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Wonderful classic harbor front hotel. Very nice front desk. Would stay again
Reviewed on May 25, 2026
Fairmont Copley Plaza, Boston
Back Bay
Price was $701, price is now $530 per person
$530
per person
Jul 26 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Wilmington (ILG) to Boston (BOS)
9/10 Wonderful! (1,241 reviews)
Gorgeous hotel in a fabulous location. Highly recommend!
Reviewed on May 19, 2026
Eurostars The Boxer
West End
Price was $672, price is now $531 per person
$531
per person
Jul 26 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Wilmington (ILG) to Boston (BOS)
8.8/10 Excellent! (1,486 reviews)
The hotel has very nice character, the room was an adequate size and the desk staff were helpful. However, our room wasn’t made up after we had been out all day and it was difficult to reach the desk to get new towels. The location was fantastic for a concert at TD Garden and they will hold your luggage if you are early for check in so that you can go out and explore the city. Overall it was a very nice stay and we would stay here again.
Reviewed on May 25, 2026
Harbor View Hotel
Save 100% on your flight
Price was $3,059, price is now $2,505 per person
$2,505
per person
Jul 27 - Jul 31
found 10 hours ago
Roundtrip flight included
New York (NYC) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,002 reviews)
The hotel location is beautiful. The building is well kept and clean. The staff was amazing! We loved our room overall but there were a few minor inconveniences:
1. The shower handle kept getting stuck and was hard to turn off.
2. We went in April and the room got very hot at night. You couldn’t change the room thermostat from hot to cold. So they told us to open the windows, which let a bee inside our room because the windows had no nets.
Reviewed on Apr 16, 2026
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See all available trips from Columbus to Massachusetts
View all trips5* Romantic vacations in Massachusetts
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $1,293, price is now $800 per person
$800
per person
Jul 26 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Wilmington (ILG) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Wonderful classic harbor front hotel. Very nice front desk. Would stay again
Reviewed on May 25, 2026
Harbor View Hotel
Save 100% on your flight
Price was $3,059, price is now $2,505 per person
$2,505
per person
Jul 27 - Jul 31
found 10 hours ago
Roundtrip flight included
New York (NYC) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,002 reviews)
The hotel location is beautiful. The building is well kept and clean. The staff was amazing! We loved our room overall but there were a few minor inconveniences:
1. The shower handle kept getting stuck and was hard to turn off.
2. We went in April and the room got very hot at night. You couldn’t change the room thermostat from hot to cold. So they told us to open the windows, which let a bee inside our room because the windows had no nets.
Reviewed on Apr 16, 2026
Wequassett Resort and Golf Club
Save 100% on your flight
Price was $2,170, price is now $1,833 per person
$1,833
per person
Jun 26 - Jun 28
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Hyannis (HYA)
9.4/10 Exceptional! (248 reviews)
From housekeeping to the front desk, the best service I've ever had.
Reviewed on Apr 26, 2026
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See all available trips from Columbus to Massachusetts
View all trips3 Night Romantic vacations in Massachusetts
Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
West End
Save 100% on your flight
Price was $1,060, price is now $784 per person
$784
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.8/10 Excellent! (1,486 reviews)
The hotel has very nice character, the room was an adequate size and the desk staff were helpful. However, our room wasn’t made up after we had been out all day and it was difficult to reach the desk to get new towels. The location was fantastic for a concert at TD Garden and they will hold your luggage if you are early for check in so that you can go out and explore the city. Overall it was a very nice stay and we would stay here again.
Reviewed on May 25, 2026
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $1,787, price is now $1,107 per person
$1,107
per person
Jul 26 - Jul 29
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Wonderful classic harbor front hotel. Very nice front desk. Would stay again
Reviewed on May 25, 2026
Don't see what you're looking for?
See all available trips from Columbus to Massachusetts
View all trips4 Night Romantic vacations in Massachusetts
Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston
Back Bay
Save 100% on your flight
Price was $1,485, price is now $1,047 per person
$1,047
per person
Jul 27 - Jul 31
found 14 hours ago
Roundtrip flight included
Kansas City (MCI) to Boston (BOS)
9/10 Wonderful! (1,241 reviews)
Gorgeous hotel in a fabulous location. Highly recommend!
Reviewed on May 19, 2026
Crowne Pointe Historic Inn & Spa - Adults Only
Save 100% on your flight
Price was $1,999, price is now $1,285 per person
$1,285
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Denver (DEN) to Provincetown (PVC)
9.2/10 Wonderful! (869 reviews)
Really cute and cozy vibe. Great location
Reviewed on Apr 19, 2026
Ellery Hotel Provincetown
Save 100% on your flight
Price was $1,653, price is now $1,207 per person
$1,207
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Denver (DEN) to Provincetown (PVC)
9.4/10 Exceptional! (421 reviews)
Very charming small facility with great rooms and support staff. I not a small block to main part of town and pier.
Reviewed on May 24, 2026
Don't see what you're looking for?
See all available trips from Columbus to Massachusetts
View all tripsHow to find a romantic Massachusetts vacation
How can I find the best Massachusetts vacation packages for couples?
To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.
How can I find cheap Massachusetts romantic packages for two?
For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.
How can I plan a great romantic trip to Massachusetts?
Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.
How much is a trip for two to Massachusetts?
Put a price on love with stunning deals for duos starting at just $514. Prices and availability are subject to change. Additional terms may apply.
Can I book Massachusetts spa packages for couples?
Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.
How can I book romantic weekend getaway packages in Massachusetts?
To book a loved-up break in Massachusetts, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).
Can I book a romantic trip to Massachusetts with free cancellation and/or flexible dates?
The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.
Why should I book my Massachusetts romantic holiday with Expedia?
If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?
Top Romantic Massachusetts Hotels
Seaport Hotel Boston
1 Seaport Lane Boston MA
$236 nightly
The price is $274 total per night from May 29 to May 30
$274 total
May 29 - May 30
Total with taxes and fees
A garden, a lobby fireplace, and premium mattresses await couples visiting this romantic hotel. The property also offers onsite dining, a terrace, and a waterfront ...
9.6/10 Exceptional! (4,371 reviews)
Couples like: onsite spa services, bar
Travelers say...
"My only complaint was that the beds were two small. My husband and two children (ages 12 and 16) stayed on two, twin beds. It would be better for any room that is to accommodate 4 people be furnished with Queen size beds."
Reviewed on May 26, 2026
Nantasket Beach Resort
45 Hull Shore Drive Hull MA
$140 nightly
The price is $156 total per night from May 27 to May 28
$156 total
May 27 - May 28
Total with taxes and fees
A hot tub and in-room fireplaces await at this romantic hotel, which also offers premium mattresses and a beachfront location.
8.6/10 Excellent! (1,003 reviews)
Couples like: hot tub, on the beach, fireplace
Travelers say...
"Locations is great!"
Reviewed on May 24, 2026
Hotel AKA Boston Common
90 Tremont St Boston MA
$283 nightly
The price is $330 total per night from May 30 to May 31
$330 total
May 30 - May 31
Total with taxes and fees
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 ...
9/10 Wonderful! (1,676 reviews)
"we love the location."
Reviewed on May 26, 2026
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 vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
