A lighthouse, rocky coastline, and a sunset over the ocean.

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

Next weekend
7 Aug - 9 Aug
In two weeks
14 Aug - 16 Aug

Our top choices for South Portland romantic hotels

Smart TV, fireplace, books

1. Private Waterfront Estate in Freeport with Fire Pit, Kayaks, & Water Views

Private Waterfront Estate in Freeport with Fire Pit, Kayaks, & Water Views
Freeport
10.0 out of 10, Exceptional, (30 reviews)
The price is AED 5,598
AED 8,070 total
includes taxes & fees
11 Aug - 12 Aug
Private Waterfront Estate in Freeport with Fire Pit, Kayaks, & Water Views
TV, fireplace

2. Waterfront Two Master Suite Penthouse with Rooftop

Waterfront Two Master Suite Penthouse with Rooftop
Downtown Portland
10.0 out of 10, Exceptional, (200 reviews)
"We’ve stayed here several times and have had a wonderful experience each time. The property was clean and comfortable and the host was very responsive. Highly recommended!"
United States
Arthur B.
The price is AED 3,753
AED 5,569 total
includes taxes & fees
8 Aug - 9 Aug
Waterfront Two Master Suite Penthouse with Rooftop
TV, stereo

3. Penthouse Two Master Waterfront Suite with Rooftop

Penthouse Two Master Waterfront Suite with Rooftop
Downtown Portland
10.0 out of 10, Exceptional, (266 reviews)
"This was one of the most spectacular places we have ever stayed. The views are amazing and the place is just incredible. We really look forward to our next visit!"
United States
Daryl R.
The price is AED 3,632
AED 5,436 total
includes taxes & fees
9 Aug - 10 Aug
Penthouse Two Master Waterfront Suite with Rooftop
Dining

4. Downtown Penthouse Suite - Stunning Harbor Views

Downtown Penthouse Suite - Stunning Harbor Views
Downtown Portland
10.0 out of 10, Exceptional, (234 reviews)
"Beautiful penthouse! Close to the harbor and all the shopping and restaurants. "
United States
Jessi F.
The price is AED 3,349
AED 4,856 total
includes taxes & fees
27 Aug - 28 Aug
Downtown Penthouse Suite - Stunning Harbor Views
Exterior detail

5. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (182 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is AED 1,091
AED 1,726 total
includes taxes & fees
1 Sep - 2 Sep
Glorious getaway on Portland's Eastern Promenade.
Exterior detail

6. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (139 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is AED 724
AED 1,141 total
includes taxes & fees
1 Sep - 2 Sep
Adorable Portland getaway on the Eastern Promenade
Beach

7. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (131 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
The price is AED 1,041
AED 1,756 total
includes taxes & fees
3 Aug - 4 Aug
City Amenities, Casco Bay Sunrises and Natural Beauty
Interior

8. 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, (81 reviews)
"Had a great time exploring Maine. Close to restaurants and "
United States
Megan N.
The price is AED 1,466
AED 2,466 total
includes taxes & fees
10 Aug - 11 Aug
Completely remodeled 2 bedroom apartment in Portland's West End
On the beach

9. AMAZING OCEANVIEW SERENITY COTTAGE 3 BED 2BATH SPECTACULAR BEACHFRONT ON OOB

AMAZING OCEANVIEW SERENITY COTTAGE 3 BED 2BATH SPECTACULAR BEACHFRONT ON OOB
Old Orchard Beach
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful beach views and direct access- we loved the beauty of the beach in winter and walking on the beach anytime we wanted, just outside our door. Lena was a gracious host and very communicative. What a wonderful place for our family gathering’. "
United States
Amy G.
The price is AED 1,469
AED 2,518 total
includes taxes & fees
2 Sep - 3 Sep
AMAZING OCEANVIEW SERENITY COTTAGE 3 BED 2BATH SPECTACULAR BEACHFRONT ON OOB
Property grounds

10. 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 AED 1,484
AED 2,146 total
includes taxes & fees
3 Aug - 4 Aug
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

Best Western Merry Manor Inn

Best Western Merry Manor Inn

10/10 Excellent
"Everything"
Thema 3-night trip
Posted 12 hours ago
Best Western Merry Manor Inn

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 Maine Mall, Willard Beach, 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 Maine Mall, Willard Beach, 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.

Explore a world of travel with Expedia