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Our top choices for Southport vacation homes

1. 1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!
1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!Bath
8.0 out of 10, Very good, (31 reviews)
The price is ¥19,165
¥28,375 total
includes taxes & fees
Nov 24 - Nov 25

2. 1920s Riverfront Cottage – Historic Maine Charm
1920s Riverfront Cottage – Historic Maine CharmEdgecomb
9.6 out of 10, Exceptional, (5 reviews)

3. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/ACGeorgetown
10.0 out of 10, Exceptional, (2 reviews)
The price is ¥33,635
¥60,875 total
includes taxes & fees
Nov 16 - Nov 17

4. 1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.
1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.Bath
8.2 out of 10, Very good, (21 reviews)
The price is ¥19,165
¥28,201 total
includes taxes & fees
Nov 26 - Nov 27

5. Mid Coast Getaway w/ water views
Mid Coast Getaway w/ water viewsWest Point
9.2 out of 10, Wonderful, (12 reviews)
The price is ¥16,770
¥31,998 total
includes taxes & fees
Nov 16 - Nov 17

6. Across the road from Pemaquid Beach: a 4-bedroom Maine home built in 1920
Across the road from Pemaquid Beach: a 4-bedroom Maine home built in 1920Pemaquid Beach
10.0 out of 10, Exceptional, (11 reviews)
The price is ¥48,712
¥104,973 total
includes taxes & fees
Nov 16 - Nov 17

7. 2 bedroom w/ expansive water views
2 bedroom w/ expansive water viewsWest Point
9.8 out of 10, Exceptional, (7 reviews)
The price is ¥20,962
¥36,219 total
includes taxes & fees
Nov 17 - Nov 18

8. Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly
Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet FriendlyBoothbay Harbor
8.0 out of 10, Very good, (2 reviews)
The price is ¥50,309
¥110,544 total
includes taxes & fees
Nov 20 - Nov 21

9. Joyful Maine Escape: A Three-Bedroom Water View Townhouse
Joyful Maine Escape: A Three-Bedroom Water View TownhouseEdgecomb
10.0 out of 10, Exceptional, (56 reviews)
The price is ¥34,497
¥63,888 total
includes taxes & fees
Nov 16 - Nov 17

10. 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, (14 reviews)
The price is ¥47,753
¥74,508 total
includes taxes & fees
Nov 17 - Nov 18

11. Captains Watch: A Coastal Escape
Captains Watch: A Coastal EscapeWest Point
8.8 out of 10, Excellent, (3 reviews)
The price is ¥24,595
¥44,048 total
includes taxes & fees
Nov 16 - Nov 17

12. Fantastic Waterfront Views
Fantastic Waterfront ViewsWest Point
9.4 out of 10, Exceptional, (24 reviews)
The price is ¥25,154
¥43,562 total
includes taxes & fees
Nov 16 - Nov 17

13. 3 Bedroom Happy Cottage 15
3 Bedroom Happy Cottage 15Edgecomb
10.0 out of 10, Exceptional, (14 reviews)
The price is ¥40,886
¥70,239 total
includes taxes & fees
Nov 16 - Nov 17

14. Ambleside in Boothbay Harbor Maine- perfect for Gardens Aglow!
Ambleside in Boothbay Harbor Maine- perfect for Gardens Aglow!Boothbay Harbor
10.0 out of 10, Exceptional, (14 reviews)
The price is ¥127,768
¥179,306 total
includes taxes & fees
Nov 17 - Nov 18

15. 2BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.
2BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.Bath
8.8 out of 10, Excellent, (29 reviews)
The price is ¥38,330
¥45,087 total
includes taxes & fees
Nov 27 - Nov 28

16. Mere Point Sunrise Views at Eastern Shore!
Mere Point Sunrise Views at Eastern Shore!Brunswick
9.8 out of 10, Exceptional, (10 reviews)
The price is ¥19,271
¥55,565 total
includes taxes & fees
Nov 16 - Nov 17

17. Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Brunswick 3BR Bungalow By Bowdoin With Fenced-In BackyardBrunswick
10.0 out of 10, Exceptional, (5 reviews)
The price is ¥39,129
¥111,588 total
includes taxes & fees
Nov 16 - Nov 17

18. Orchid Harbor, Bailey Island 3BR
Orchid Harbor, Bailey Island 3BRHarpswell
10.0 out of 10, Exceptional, (13 reviews)
The price is ¥26,322
¥63,138 total
includes taxes & fees
Dec 13 - Dec 14

19. Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Private Home w/ Office Year Round in town Brunswick next to BowdoinBrunswick
8.8 out of 10, Excellent, (28 reviews)
The price is ¥26,352
¥63,715 total
includes taxes & fees
Dec 1 - Dec 2

20. Classic New England Waterfront House Big Lawn Beautiful Sunrise
Classic New England Waterfront House Big Lawn Beautiful SunriseHarpswell
10.0 out of 10, Exceptional, (2 reviews)
The price is ¥55,899
¥243,370 total
includes taxes & fees
Nov 30 - Dec 1
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.
Learn more about Southport
Nestled on a picturesque island, this coastal gem invites visitors to explore Hendricks Head Beach and its historic lighthouse. Spend your days enjoying fresh seafood at local restaurants, visiting the Hendricks Hill Museum, or taking a short trip to nearby Boothbay Harbor Marina.

Photo by Melissa Hoyer
Open Photo by Melissa Hoyer
Top reviews in Southport

Harborage Inn on the Oceanfront
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