Find Romantic Hotels in South Portland, ME

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on South Portland Romantic Hotels

Our top choices for South Portland romantic hotels

Exterior detail

Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (78 reviews)
"Lovely unit. Very comfortable bed. Nice to have off street parking. Walkable to Old Port. Would def stay again. "
United States
Erin H.
The price is ￥28,593
￥84,356 total
includes taxes & fees
Jun 4 - Jun 5
Elegant condo - walk to Portland's best restaurants & Old Port
Property grounds

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (37 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is ￥24,145
￥78,378 total
includes taxes & fees
Jun 4 - Jun 5
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Exterior detail

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (132 reviews)
"The host was very friendly and it was an easy apartment to check into. "
United States
Kendall M.
The price is ￥31,293
￥49,693 total
includes taxes & fees
Jun 1 - Jun 2
Adorable Portland getaway on the Eastern Promenade
Property grounds

Waterfront Private Apartment, minutes from LLBean!

Waterfront Private Apartment, minutes from LLBean!
Freeport
10.0 out of 10, Exceptional, (17 reviews)
"The room was clean and the area is great for walking with the dog."
United States
Anonymous traveler
The price is ￥43,199
￥67,274 total
includes taxes & fees
Jun 7 - Jun 8
Waterfront Private Apartment, minutes from LLBean!
Interior

Completely remodeled 2 bedroom apartment in Portland's West End

Completely remodeled 2 bedroom apartment in Portland's West End
West End
10.0 out of 10, Exceptional, (78 reviews)
"Had a great time exploring Maine. Close to restaurants and "
United States
Megan N.
The price is ￥63,381
￥105,792 total
includes taxes & fees
Jun 1 - Jun 2
Completely remodeled 2 bedroom apartment in Portland's West End
Exterior detail

Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (174 reviews)
"Very cute and comfy. We would definitely stay here again. "
United States
Marie s.
The price is ￥51,944
￥79,994 total
includes taxes & fees
Jun 1 - Jun 2
Glorious getaway on Portland's Eastern Promenade.
Interior

Old Port Penthouse Suite - Amazing Harbor Views

Old Port Penthouse Suite - Amazing Harbor Views
Downtown Portland
10.0 out of 10, Exceptional, (251 reviews)
"We loved our stay and will definitely book again the next time we come to Portland. The location is perfect - right in the middle of restaurants and just a short block’s walk to Fore St. for shopping. We loved the relaxing design of the apartment, and the views did not disappoint. Can’t wait to go back!"
United States
Barbara K.
The price is ￥95,930
￥149,235 total
includes taxes & fees
May 25 - May 26
Old Port Penthouse Suite - Amazing Harbor Views
TV, stereo

Penthouse Two Master Waterfront Suite with Rooftop

Penthouse Two Master Waterfront Suite with Rooftop
Downtown Portland
10.0 out of 10, Exceptional, (261 reviews)
"Great location & view"
United States
tina n.
The price is ￥113,403
￥180,747 total
includes taxes & fees
Jun 1 - Jun 2
Penthouse Two Master Waterfront Suite with Rooftop
On the beach

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Old Orchard Beach
9.6 out of 10, Exceptional, (69 reviews)
"Stunning views and a wonderful property to celebrate Christmas with our family! The pool table was a huge hit. Thank you Jason and your team for your hospitality and responsiveness!"
United States
Linda S.
The price is ￥118,979
￥227,342 total
includes taxes & fees
Jun 3 - Jun 4
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Property grounds

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is ￥71,340
￥100,962 total
includes taxes & fees
May 24 - May 25
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
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.
View all properties

Top South Portland Hotel Reviews

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

6/10 Okay
"We’ve stayed at this hotel 5 times now and have always enjoyed the historic charm and location. Check-in during this stay went smoothly, however we were disappointed when we arrived to find the toilet in our room was dirty. We also asked the front desk if the TVs allowed streaming services like Netflix or Prime Video, and the girl at the front responded rather rudely that “we are a historic hotel, so we do not offer smart TVs.” We completely understand preserving the character of a historic property, but the response came across dismissive for what was just a simple question. We were also told that because parts of the hotel are older, some areas may not look as clean compared to newer hotels. While we appreciate the history and character of the property, cleanliness and customer service should still meet expectations regardless of the building’s age. We’ve enjoyed staying here in the past, which makes this visit more disappointing, and we hope these issues are addressed moving forward."
Lauren 1-night trip
Posted 11 hours ago
Portland Regency Hotel & Spa

Frequently asked questions

Searching for romantic hotels in South Portland?
Are you looking for a romantic vacation? Our guests also love South Portland for its major shopping area, array of dining options, and sporting events. If you'd like to explore some of the area's notable sights, you might make a stop by Willard Beach, Maine Mall, or Casco Bay. If you're interested in staying near a certain attraction, you can sort by neighborhood or distance to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to South Portland?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in South Portland: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 30°F. The snowiest months in South Portland are January, March, February, and December, with each month seeing an average of 7 inches of snowfall.
What is there to do in South Portland?
There's nothing better than experiencing a new destination with your sweetheart, so consider checking out all that South Portland has to offer. Couples looking for a little of everything will enjoy South Portland for its shopping, restaurants, and sporting events. You might consider a visit to Willard Beach, Maine Mall, or Casco Bay.
What's the best way to get to South Portland and around town during my romantic getaway?
These transportation options in South Portland might help your romantic getaway go off without a hitch: To get to South Portland, book a flight to Portland Intl. Jetport Airport (PWM), which is the closest major airport, located 3.5 mi (5.7 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.