Highland Hotels, South Portland

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Highland hotels

Property amenity
Best Western Merry Manor Inn

Best Western Merry Manor Inn

Best Western Merry Manor Inn
2.5 star property
Highland
9.0 out of 10, Wonderful, (1002)
"The room was clean and the bed very comfortable. The breakfast was great. We will definitely stay here on our next visit to Portland. "
United States
Pamela
The price is NZ$184
includes taxes & fees
29 Dec - 30 Dec
Best Western Merry Manor Inn
Restaurant
Germaine Inn South Portland

Germaine Inn South Portland

Germaine Inn South Portland
2.0 star property
Thorton Heights, 1.6 km from Highland
7.6 out of 10, Good, (403)
"Amazing price, clean comfortable room, heated pool, free breakfast. "
United States
Sue
The price is NZ$125
includes taxes & fees
31 Dec - 1 Jan 2026
Germaine Inn South Portland
Exterior
Long Creek Hotel by IHG

Long Creek Hotel by IHG

Long Creek Hotel by IHG
2.5 star property
4.2 km from Highland
7.4 out of 10, Good, (1001)
"Great place to stay "
United States
Mario
The price is NZ$143
includes taxes & fees
18 Dec - 19 Dec
Long Creek Hotel by IHG
Aerial view
Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront
3.0 star property
6.1 km from Highland
9.2 out of 10, Wonderful, (1008)
"Great staff and a surprisingly great free breakfast."
United States
Paul
The price is NZ$182
includes taxes & fees
23 Dec - 24 Dec
Hilton Garden Inn Portland Downtown Waterfront
Lounge
Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square
3.0 star property
5.7 km from Highland
9.0 out of 10, Wonderful, (1293)
"Room was great, awesome location!"
United States
Erick
The price is NZ$185
includes taxes & fees
11 Jan - 12 Jan 2026
Hyatt Place Portland Downtown - Old Port Square
Reception
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area
2.5 star property
4.7 km from Highland
8.8 out of 10, Excellent, (1660)
"Staff was friendly and hotel was clean."
United States
Dianna
The price is NZ$125
includes taxes & fees
11 Jan - 12 Jan 2026
Tru by Hilton Portland Airport Area
Premium bedding, desk, blackout curtains, iron/ironing board
Portland Harbor Hotel

Portland Harbor Hotel

Portland Harbor Hotel
4.0 star property
5.6 km from Highland
9.2 out of 10, Wonderful, (1713)
"Beautiful room, friendly staff, and perfect location."
United States
Lisa
The price is NZ$270
includes taxes & fees
18 Dec - 19 Dec
Portland Harbor Hotel
Property entrance
Aloft Portland Downtown Waterfront ME

Aloft Portland Downtown Waterfront ME

Aloft Portland Downtown Waterfront ME
3.0 star property
5.2 km from Highland
8.8 out of 10, Excellent, (1005)
"Clean, good breakfast and nice bar! "
United States
James
The price is NZ$151
includes taxes & fees
12 Jan - 13 Jan 2026
Aloft Portland Downtown Waterfront ME
Suite, 2 Bedrooms | Private kitchenette
Residence Inn Portland Downtown/Waterfront

Residence Inn Portland Downtown/Waterfront

Residence Inn Portland Downtown/Waterfront
3.0 star property
6.5 km from Highland
8.8 out of 10, Excellent, (1003)
"Clean, friendly staff, prompt shuttle service, good breakfasts"
United States
Brandy Morris
The price is NZ$151
includes taxes & fees
4 Jan - 5 Jan 2026
Residence Inn Portland Downtown/Waterfront
Lobby
Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

Comfort Inn South Portland Airport
2.5 star property
4.9 km from Highland
8.6 out of 10, Excellent, (1875)
"Clean room, friendly staff, good breakfast"
United States
Shaun
The price is NZ$142
includes taxes & fees
21 Dec - 22 Dec
Comfort Inn South Portland Airport
Exterior
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront
2.5 star property
6.2 km from Highland
8.8 out of 10, Excellent, (1006)
"Clean, comfortable and convenient location."
United States
Kurt
The price is NZ$176
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn Portland Downtown - Waterfront
Exterior
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
3.0 star property
5 km from Highland
8.8 out of 10, Excellent, (2284)
"Great breakfast options and very convenient location."
United States
Greta
The price is NZ$153
includes taxes & fees
30 Dec - 31 Dec
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Exterior
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine
3.5 star property
4.8 km from Highland
9.4 out of 10, Exceptional, (1135)
"Room was spotless and the staff was extremely friendly and knowledgeable! Would definitely stay here again!"
United States
Lori ann
The price is NZ$178
includes taxes & fees
11 Jan - 12 Jan 2026
Embassy Suites by Hilton Portland Maine
Exterior
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG
4.0 star property
5.3 km from Highland
8.8 out of 10, Excellent, (1433)
"Every thing was perfect, service, accomodations, and friendly staff!!!"
United States
Michael
The price is NZ$142
includes taxes & fees
18 Dec - 19 Dec
Holiday Inn Portland-By the Bay by IHG
Tapas bar
AC Hotel Portland Downtown/Waterfront, ME

AC Hotel Portland Downtown/Waterfront, ME

AC Hotel Portland Downtown/Waterfront, ME
3.5 star property
6.4 km from Highland
9.2 out of 10, Wonderful, (1003)
"The amenities and location "
United States
Michael
The price is NZ$166
includes taxes & fees
21 Dec - 22 Dec
AC Hotel Portland Downtown/Waterfront, ME
Standard Room, 1 King Bed, Non Smoking
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port
3.0 star property
6.5 km from Highland
9.4 out of 10, Exceptional, (1134)
"Super modern, super clean, super friendly staff, love Cambria hotels"
United States
Robert
The price is NZ$236
includes taxes & fees
5 Jan - 6 Jan 2026
Cambria Hotel Portland Downtown-Old Port
Terrace/patio
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa
3.5 star property
5.9 km from Highland
9.4 out of 10, Exceptional, (1551)
"Yes, excellent service and we really enjoyed our stay."
United States
Bruce
Portland Regency Hotel & Spa
View from property
The Westin Portland Harborview

The Westin Portland Harborview

The Westin Portland Harborview
4.0 star property
5.3 km from Highland
8.8 out of 10, Excellent, (1002)
"Helpful and friendly staff"
United States
Wei Chien
The price is NZ$170
includes taxes & fees
5 Jan - 6 Jan 2026
The Westin Portland Harborview
Front of property – evening/night
Inn at St John Portland In-Town

Inn at St John Portland In-Town

Inn at St John Portland In-Town
2.5 star property
4.8 km from Highland
8.8 out of 10, Excellent, (1142)
"Friendly helpful staff and a nice independent location "
United States
Robert
The price is NZ$150
includes taxes & fees
15 Jan - 16 Jan 2026
Inn at St John Portland In-Town
Outdoor pool
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland
4.0 star property
4.7 km from Highland
8.0 out of 10, Very good, (1314)
"Clean and comfortable room, nice staff"
United States
Angie
The price is NZ$139
includes taxes & fees
15 Jan - 16 Jan 2026
DoubleTree by Hilton Hotel Portland
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

Our guide on where to stay in Highland

Find the best Highland areas for the activities you enjoy most.

Willard Beach

When in Willard Beach, you can plan a visit to Willard Beach and Fort Preble, some noteworthy sights in the nearby area.

Ferry Village

While Ferry Village isn't home to many top sights, Willard Beach and Casco Bay Lines Ferry Terminal are some notable places to visit nearby.

Knightville

While Knightville isn't home to many top sights, Victoria Mansion and Casco Bay Bridge are some notable places to visit nearby.

Meetinghouse Hill

While Meetinghouse Hill may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Willard Beach and Victoria Mansion.

Willard

Willard might not have many top sights, but Willard Beach and Victoria Mansion are two attractions nearby that you can check out.

Top Highland Hotel Reviews

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent
"Everything was great to check in until departure. Staff was friendly and helpful. At check out I left my boot a in the room, called and told them that I would be back to get them and the put them in a bag and had them ready for me. Room was comfy and a good size."
Mary Rose 1-night trip
Posted 2 days ago
Hampton Inn Portland Downtown - Waterfront

Explore a world of travel with Expedia

Frequently asked questions

What is Highland like?
Guests are sure to enjoy their time checking out all that South Portland's Highland neighbourhood has to offer. Consider a visit to Casco Bay as part of your Highland travel plans.
What's a favourite place to stay in Highland?
Based on Expedia customer reviews, Best Western Merry Manor Inn is the highest ranked property in Highland. This hotel offers free breakfast and an outdoor pool.
If I need to cancel my hotel reservation in Highland, will I receive a refund?
Yes! You'll find that most hotel room reservations are fully refundable if you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to cancel it and receive a refund within a 24-hour period of your booking. Enter your dates, click on "Search", then use the "fully refundable" filter to view the best options available in Highland.
What are the top things to see and do in Highland?
Casco Bay is an attraction you might want to check out while you're in Highland. While you're out sightseeing in South Portland, make sure that you visit other sights such as Maine Military Museum or The Cheese Iron.