Cuckold Lighthouse built in 1896 at the entrance to Boothbay Harbor visible from the tip of Southport Island

Holiday Homes in Southport

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Southport holiday homes

Property grounds

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
7.6 out of 10, Good, (14 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
The price is NZ$286
includes taxes & fees
17 June - 18 June
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Outdoor dining

Captain's Guest Room. Authenticity. Value. Near everything. No fees.

Captain's Guest Room. Authenticity. Value. Near everything. No fees.
Bath
8.2 out of 10, Very good, (22 reviews)
"Great location and a beautiful property. Great walking/driving distance from town and the waterfront, we had a great stay and would do it again! "
United States
Nina P.
The price is NZ$250
includes taxes & fees
22 June - 23 June
Captain's Guest Room. Authenticity. Value. Near everything. No fees.
Interior

3 Bedroom Happy Cottage 15

3 Bedroom Happy Cottage 15
Edgecomb
10.0 out of 10, Exceptional, (6 reviews)
"Great property with central location in mid coast Maine. Beautifully decorated with very comfortable beds! Jeff was great with communication throughout to ensure we had everything we needed! Would stay again! "
United States
Decourcey D.
The price is NZ$785
includes taxes & fees
17 June - 18 June
3 Bedroom Happy Cottage 15
Smart TV

Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home

Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home
Pemaquid Beach
10.0 out of 10, Exceptional, (8 reviews)
"Comfortable, clean and beautiful "
United States
Corina
The price is NZ$1,165
includes taxes & fees
21 June - 22 June
Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home
TV

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.4 out of 10, Exceptional, (6 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is NZ$423
includes taxes & fees
20 June - 21 June
Mid Coast Getaway w/ water views
Terrace/patio

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is NZ$618
includes taxes & fees
17 June - 18 June
Camp Forever cottage
Iron/ironing board, travel cot, WiFi, bed sheets

Fully Renovated "Saltbox" Home in Boothbay

Fully Renovated "Saltbox" Home in Boothbay
Boothbay
The price is NZ$953
includes taxes & fees
18 June - 19 June
Fully Renovated "Saltbox" Home in Boothbay
Property grounds

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (61 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
The price is NZ$807
includes taxes & fees
20 June - 21 June
Centerview cottage
Terrace/patio

Tide Haven Cottage on Bay Point

Tide Haven Cottage on Bay Point
Georgetown
The price is NZ$986
includes taxes & fees
1 July - 2 July
Tide Haven Cottage on Bay Point
TV

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is NZ$814
includes taxes & fees
16 July - 17 July
2 bedroom w/ expansive water views
Interior

Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2

Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2
Brunswick
The price is NZ$938
includes taxes & fees
18 June - 19 June
Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2
Property grounds

Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, 2-Story Cottage, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (29 reviews)
"Enjoyed the place, great location. "
United States
Erik P.
Boothbay Harbor, 2-Story Cottage, downtown
Beach

Pemaquid Escape | Curated Comfort + Hot Tub

Pemaquid Escape | Curated Comfort + Hot Tub
Walpole
10.0 out of 10, Exceptional, (3 reviews)
"The place was beautiful, with charming and had perfect design choices. Check in was so convenient, and the hosts were quite responsive to any needs. We all felt so comfortable there. It felt private, yet was conveniently located to Damariscotta. I would absolutely rent here again."
United States
Tera P.
The price is NZ$1,160
includes taxes & fees
17 June - 18 June
Pemaquid Escape | Curated Comfort + Hot Tub
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (52 reviews)
"Wonderful stay!"
United States
Erika T.
The price is NZ$624
includes taxes & fees
22 June - 23 June
Full sized home
Smart TV

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (5 reviews)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is NZ$832
includes taxes & fees
24 June - 25 June
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Property grounds

Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
9.8 out of 10, Exceptional, (10 reviews)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
Orchid Harbor, Bailey Island 3BR
Interior

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Brunswick
10.0 out of 10, Exceptional, (2 reviews)
"Great location"
United States
Ashley W.
The price is NZ$1,244
includes taxes & fees
17 June - 18 June
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Desk, iron/ironing board, free WiFi, bed sheets

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Georgetown
10.0 out of 10, Exceptional, (2 reviews)
"Really lovely cabin with all the amenities within a stone’s throw to amazing trails and beaches. Would love to come back!"
United States
Palmer M.
The price is NZ$800
includes taxes & fees
28 June - 29 June
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Fridge, microwave, oven, stovetop

Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
Bath
10.0 out of 10, Exceptional, (9 reviews)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is NZ$1,267
includes taxes & fees
24 June - 25 June
Award Winning Luxury Carriage House a short stroll from town!
Interior

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
9.0 out of 10, Wonderful, (27 reviews)
"Perfect spot for us to spend a weekend up at Bowdoin where "
United States
Michaela M.
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
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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Top Southport Hotel Reviews

Fishermans Wharf Inn

Fishermans Wharf Inn

10/10 Excellent
"Such a lovely hotel with an excellent staff and the most convenient location. It was a truly delightful stay."
JIll 2-night trip
Posted less than an hour ago
Fishermans Wharf Inn

Find out more about Southport

Southport Holiday Homes information

Number of reviews
284
Accommodation
496 Holiday Homes
Lowest Price
NZ$250
Highest Price
NZ$1,267