Photo by Melissa Hoyer

Holiday Homes in Southport

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Our top choices for Southport holiday 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)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is NZ$319
includes taxes & fees
24 Nov - 25 Nov
1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!

2. 1920s Riverfront Cottage – Historic Maine Charm

1920s Riverfront Cottage – Historic Maine Charm
Edgecomb
9.6 out of 10, Exceptional, (5 reviews)
"This cottage is the perfect blend of historic charm and modern upgrades. The view of the river is incredible, and the secluded location is just a short drive from downtown Wiscasset and Edgecomb. The sunroom is already a great place to hang out and enjoy the river view, but the owners are also putting in a lot of work to create an enjoyable outdoor space. Jeffrey is easy to work with and honestly wants you to have a good stay."
United States
Shelly
The price is NZ$593
includes taxes & fees
10 Nov - 11 Nov
1920s Riverfront Cottage – Historic Maine Charm

3. 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$668
includes taxes & fees
10 Nov - 11 Nov
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

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)
"Cute but aging small space, Near attractions"
United States
michael
The price is NZ$338
includes taxes & fees
26 Nov - 27 Nov
1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.

5. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is NZ$367
includes taxes & fees
12 Nov - 13 Nov
Mid Coast Getaway w/ water views

6. Charming Historic home steps away from downtown

Charming Historic home steps away from downtown
Bath
9.4 out of 10, Exceptional, (3 reviews)
"The communication was excellent. The location was excellent."
United States
Holly Y.
The price is NZ$1,115
includes taxes & fees
17 Nov - 18 Nov
Charming Historic home steps away from downtown

7. 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 Friendly
Boothbay Harbor
8.0 out of 10, Very good, (2 reviews)
"Ok Beautiful location price was on the high side but very clean and state of the art."
United States
Steve R.
The price is NZ$1,229
includes taxes & fees
20 Nov - 21 Nov
Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly

8. 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 1920
Pemaquid Beach
10.0 out of 10, Exceptional, (11 reviews)
"Comfortable, clean and beautiful "
United States
Corina
The price is NZ$1,152
includes taxes & fees
15 Nov - 16 Nov
Across the road from Pemaquid Beach: a 4-bedroom Maine home built in 1920

9. 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)
"Another great stay by a great host. The host Jared even provided some activities for our granddaughters to do while we were on vacation. You will not be disappointed with this property. Looking to stay there again in the future. Thank you, Jared!"
United States
Ronald H.
The price is NZ$828
includes taxes & fees
15 Nov - 16 Nov
Award Winning Luxury Carriage House a short stroll from town!

10. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
9.8 out of 10, Exceptional, (7 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$417
includes taxes & fees
17 Nov - 18 Nov
2 bedroom w/ expansive water views

11. 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 house is incredible! We loved our stay here. It was the perfect location to explore Boothbay. They had ALL needed amenities, even firewood. The beds were super comfortable and the house is very spacious. We would definitely stay here again."
United States
Allison W.
The price is NZ$1,935
includes taxes & fees
10 Nov - 11 Nov
Ambleside in Boothbay Harbor Maine- perfect for Gardens Aglow!

12. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
8.8 out of 10, Excellent, (3 reviews)
"Such a beautiful stay!! My whole group wished we could have stayed longer. We plan to come back"
United States
Holly G.
The price is NZ$496
includes taxes & fees
15 Nov - 16 Nov
Captains Watch: A Coastal Escape

13. Joyful Maine Escape: A Three-Bedroom Water View Townhouse

Joyful Maine Escape: A Three-Bedroom Water View Townhouse
Edgecomb
10.0 out of 10, Exceptional, (56 reviews)
"This was a very nice home. Clean, comfortable, and lovely. The water views are great, too."
United States
kathleen m.
The price is NZ$710
includes taxes & fees
10 Nov - 11 Nov
Joyful Maine Escape: A Three-Bedroom Water View Townhouse

14. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.4 out of 10, Exceptional, (23 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is NZ$502
includes taxes & fees
10 Nov - 11 Nov
Fantastic Waterfront Views

15. 3 Bedroom Happy Cottage 15

3 Bedroom Happy Cottage 15
Edgecomb
10.0 out of 10, Exceptional, (14 reviews)
"A great property and easy process."
United States
Dan L.
The price is NZ$802
includes taxes & fees
10 Nov - 11 Nov
3 Bedroom Happy Cottage 15

16. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is NZ$627
includes taxes & fees
10 Nov - 11 Nov
Orchid Harbor, Bailey Island 3BR

17. 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)
"Nice place for the money spent"
United States
Kevin P.
2BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.

18. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is NZ$642
includes taxes & fees
16 Nov - 17 Nov
Mere Point Sunrise Views at Eastern Shore!

19. 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, (5 reviews)
"Great location and super clean house"
United States
Gary R.
The price is NZ$1,235
includes taxes & fees
10 Nov - 11 Nov
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

20. 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
8.8 out of 10, Excellent, (28 reviews)
"Perfect spot for us to spend a weekend up at Bowdoin where "
United States
Michaela M.
The price is NZ$722
includes taxes & fees
1 Dec - 2 Dec
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.

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 Harbour Marina.

A lighthouse on a rocky outcrop with a rainbow in the sky.
Photo by Melissa Hoyer
Open Photo by Melissa Hoyer

Top reviews in Southport