A lighthouse on a rocky island with waves crashing against it.

Holiday Homes in Southport

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Southport holiday homes

A garden with hydrangea flowers, a wooden chair, and a "NO PARKING" sign.

1. Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, 2-Story Cottage, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (30 reviews)
"Location, location, location! We stayed for 4 days and didn't have to drive ONCE. David was easy to communicate with and very helpful. House was clean and comfortable. Would definitely stay again!"
United States
Justin T.
The price is NZ$620
includes taxes & fees
19 Oct - 20 Oct
Boothbay Harbor, 2-Story Cottage, downtown
A treehouse with a wooden staircase and a small building with a colorful mural.

2. Perfect stopover, getaway, base to explore the area, or to simply stay in town.

Perfect stopover, getaway, base to explore the area, or to simply stay in town.
Bath
8.0 out of 10, Very good, (30 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$310
includes taxes & fees
26 Sept - 27 Sept
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
A wooden staircase leading to a stone entrance of a building surrounded by trees.

3. Fully Renovated "Saltbox" Home in Boothbay

Fully Renovated "Saltbox" Home in Boothbay
Boothbay
The price is NZ$985
includes taxes & fees
28 Sept - 29 Sept
Fully Renovated "Saltbox" Home in Boothbay
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

4. 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)
The price is NZ$694
includes taxes & fees
25 Oct - 26 Oct
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
A wooden staircase with a wooden railing, surrounded by green foliage.

5. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is NZ$321
includes taxes & fees
25 Sept - 26 Sept
1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
A wooden deck with a view of a lake and trees.

6. 1920s Riverfront Cottage – Historic Maine Charm

1920s Riverfront Cottage – Historic Maine Charm
Edgecomb
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful spot. Make sure to use the hot tub!"
United States
Sam D.
The price is NZ$701
includes taxes & fees
28 Sept - 29 Sept
1920s Riverfront Cottage – Historic Maine Charm
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

7. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (10 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$352
includes taxes & fees
29 Sept - 30 Sept
Mid Coast Getaway w/ water views
A modern kitchen with white cabinetry, stainless steel appliances, and a granite countertop.

8. Boothbay Harbor, The Francis Greene House, downtown

Boothbay Harbor, The Francis Greene House, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (52 reviews)
"Host communication was excellent. Location was ideal, walkable to the Boothbay Harbor attractions. Nice new wooden floors upstairs with the bedrooms. No AC which was fine for our stay. We must have stayed the first of the season, as the negatives were related to this. The toilets were disgusting with a foul odor and green mold on toilet seats, presumably from 9 months of zero use and the maids not cleaning prior to our arrival. Either way they should be replaced. All else with home was fine."
United States
Timothy M.
The price is NZ$1,307
includes taxes & fees
11 Oct - 12 Oct
Boothbay Harbor, The Francis Greene House, downtown
A rocking chair and a small table with a decorative plate, both placed on a wooden deck in front of a red building with a white door.

9. 2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.

2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
Bath
9.0 out of 10, Wonderful, (27 reviews)
"Clean, walkable to town, nice backyard to sit and talk."
United States
Kathleen
The price is NZ$415
includes taxes & fees
28 Sept - 29 Sept
2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

10. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (5 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$484
includes taxes & fees
29 Sept - 30 Sept
2 bedroom w/ expansive water views
A two-story white house with a front porch, green shutters, and a covered patio area with chairs.

11. Charming Historic home steps away from downtown

Charming Historic home steps away from downtown
Bath
9.0 out of 10, Wonderful, (2 reviews)
"The communication was excellent. The location was excellent."
United States
Holly Y.
The price is NZ$1,303
includes taxes & fees
6 Oct - 7 Oct
Charming Historic home steps away from downtown
A lakeside property with a deck, picnic table, and barbecue grill.

12. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (68 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is NZ$628
includes taxes & fees
7 Oct - 8 Oct
Camp Forever cottage
A deck with outdoor furniture, a table, and chairs, overlooking a body of water and buildings.

13. 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
6.0 out of 10, (1 review)
"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$1,455
includes taxes & fees
17 Oct - 18 Oct
Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly
A modern kitchen with stainless steel appliances, wooden bar stools, and a large window providing natural light.

14. Ambleside in Boothbay Harbor Maine- perfect for your Maine coastal vacation!

Ambleside in Boothbay Harbor Maine- perfect for your Maine coastal vacation!
Boothbay Harbor
10.0 out of 10, Exceptional, (13 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$2,065
includes taxes & fees
18 Oct - 19 Oct
Ambleside in Boothbay Harbor Maine- perfect for your Maine coastal vacation!
A cozy room with a window seat by a large window overlooking a body of water. A lamp and a book are placed on the seat.

15. Classic Maine Waterfront Home on the Back River – Trevett

Classic Maine Waterfront Home on the Back River – Trevett
Boothbay
6.0 out of 10, (1 review)
"We stayed for 2 nights. Upon arriving we immediately noticed mouse traps in every room which was a little unnerving; however, there did not appear to be evidence of live mice in the house. The towels did not smell fresh in downstairs bathroom. And the water pressure was terrible. If the downstairs water was running, there was no water in sink upstairs. There were no bed slats in one bed causing the mattress to fall on floor. Additionally, when we returned one evening, I notified host...
United States
Blanche H.
The price is NZ$1,543
includes taxes & fees
8 Oct - 9 Oct
Classic Maine Waterfront Home on the Back River – Trevett
A wooden deck with a view of a lake, a small building, and surrounding trees.

16. 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, (54 reviews)
"Great location for a trip up the Maine coast. "
United States
Steve M.
The price is NZ$689
includes taxes & fees
25 Oct - 26 Oct
Joyful Maine Escape: A Three-Bedroom Water View Townhouse
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

17. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (20 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is NZ$372
includes taxes & fees
28 Sept - 29 Sept
Fantastic Waterfront Views
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

18. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is NZ$377
includes taxes & fees
28 Sept - 29 Sept
Captains Watch: A Coastal Escape
A wooden deck with a view of a lake, surrounded by trees and shrubs.

19. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (73 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
The price is NZ$805
includes taxes & fees
28 Sept - 29 Sept
Centerview cottage
A spacious living area with a wooden ceiling, a dining table with chairs, and a kitchen area with white cabinets.

20. 3 Bedroom Happy Cottage 15

3 Bedroom Happy Cottage 15
Edgecomb
10.0 out of 10, Exceptional, (13 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$920
includes taxes & fees
5 Oct - 6 Oct
3 Bedroom Happy Cottage 15
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

Flagship Inn and Suites

Flagship Inn and Suites

10/10 Excellent
"They were very accomadating.Staff was very friendly.Beds were very comfortable.Every thing was clean.It was nice to walk next door for breakfast.Plenty of parking and close to your room."
Sheryl 2-night trip
Posted 6 hours ago
Flagship Inn and Suites

Find out more about Southport

Southport Holiday Homes information

Number of reviews
416
Accommodation
622 Holiday Homes
Lowest Price
NZ$310
Highest Price
NZ$2,065