Photo by Melissa Hoyer

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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)
"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 ¥19,165
¥28,375 total
includes taxes & fees
Nov 24 - Nov 25
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)
"We had a wonderful stay at the cottage. It is small (at least for 4 people), but cozy, sparkling clean, and freshly renovated, with everything you need and wonderful views of the river. Jeffrey, our host, made us feel welcome at every step and was consistently attentive and thoughtful. Close to hiking trails, dining and shopping, and the stunning Maine Coastal Botanical gardens."
United States
Laure K.
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 ¥33,635
¥60,875 total
includes taxes & fees
Nov 16 - Nov 17
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 ¥19,165
¥28,201 total
includes taxes & fees
Nov 26 - Nov 27
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 ¥16,770
¥31,998 total
includes taxes & fees
Nov 16 - Nov 17
Mid Coast Getaway w/ water views

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

7. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
9.8 out of 10, Exceptional, (7 reviews)
"One of the best property rentals that I’ve stayed in the West Point area of Phippsburg - views were spectacular and the newly renovated house was perfect."
United States
Mally G.
The price is ¥20,962
¥36,219 total
includes taxes & fees
Nov 17 - Nov 18
2 bedroom w/ expansive water views

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 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 ¥50,309
¥110,544 total
includes taxes & fees
Nov 20 - Nov 21
Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly

9. 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)
"What a beautiful, clean, and well-appointed home! The views were gorgeous. Host communications on home details and directions were clear and helpful. We had a lovely stay."
United States
Mary K.
The price is ¥34,497
¥63,888 total
includes taxes & fees
Nov 16 - Nov 17
Joyful Maine Escape: A Three-Bedroom Water View Townhouse

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)
"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 ¥47,753
¥74,508 total
includes taxes & fees
Nov 17 - Nov 18
Award Winning Luxury Carriage House a short stroll from town!

11. 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 ¥24,595
¥44,048 total
includes taxes & fees
Nov 16 - Nov 17
Captains Watch: A Coastal Escape

12. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.4 out of 10, Exceptional, (24 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is ¥25,154
¥43,562 total
includes taxes & fees
Nov 16 - Nov 17
Fantastic Waterfront Views

13. 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 ¥40,886
¥70,239 total
includes taxes & fees
Nov 16 - Nov 17
3 Bedroom Happy Cottage 15

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 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 ¥127,768
¥179,306 total
includes taxes & fees
Nov 17 - Nov 18
Ambleside in Boothbay Harbor Maine- perfect for Gardens Aglow!

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)
"Nice place for the money spent"
United States
Kevin P.
The price is ¥38,330
¥45,087 total
includes taxes & fees
Nov 27 - Nov 28
2BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.

16. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"This little spot was an ideal getaway for our family’s summer trip to Maine. We very much enjoyed the porch with a view of the water and felt right at home here."
United States
James C.
The price is ¥19,271
¥55,565 total
includes taxes & fees
Nov 16 - Nov 17
Mere Point Sunrise Views at Eastern Shore!

17. 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 ¥39,129
¥111,588 total
includes taxes & fees
Nov 16 - Nov 17
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

18. 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 ¥26,322
¥63,138 total
includes taxes & fees
Dec 13 - Dec 14
Orchid Harbor, Bailey Island 3BR

19. 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 ¥26,352
¥63,715 total
includes taxes & fees
Dec 1 - Dec 2
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

20. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! "
United States
Ashma B.
The price is ¥55,899
¥243,370 total
includes taxes & fees
Nov 30 - Dec 1
Classic New England Waterfront House Big Lawn Beautiful Sunrise
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.

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