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

Southport Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Southport vacation rentals

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 AED 1,653
AED 2,502 total
includes taxes & fees
23 Jul - 24 Jul
Award Winning Luxury Carriage House a short stroll from town!
Interior

Vacation Creation Downtown Brunswick 2King Beds

Vacation Creation Downtown Brunswick 2King Beds
Brunswick
9.6 out of 10, Exceptional, (19 reviews)
"Easy to rent."
United States
Alan B.
The price is AED 918
AED 1,894 total
includes taxes & fees
23 Jun - 24 Jun
Vacation Creation Downtown Brunswick 2King Beds
Property grounds

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (62 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 AED 1,084
AED 1,758 total
includes taxes & fees
23 Jun - 24 Jun
Centerview cottage
House (2 Bedrooms) | Interior

1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is AED 500
AED 1,242 total
includes taxes & fees
16 Jul - 17 Jul
1 Mi to Maine Street! Mcm-style Home in Brunswick
Fridge, microwave, oven, stovetop

Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
East Boothbay
10.0 out of 10, Exceptional, (48 reviews)
"Excellent, clean property. "
United States
Andy H.
The price is AED 1,041
AED 2,196 total
includes taxes & fees
26 Jun - 27 Jun
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
1 bedroom, iron/ironing board, bed sheets

Cheerful Cottage Close to Everything 13

Cheerful Cottage Close to Everything 13
Edgecomb
9.2 out of 10, Wonderful, (17 reviews)
"Nice and quiet even though it was right next to major travel routes "
United States
Gary
The price is AED 613
AED 1,162 total
includes taxes & fees
10 Jul - 11 Jul
Cheerful Cottage Close to Everything 13
Interior

2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick
Brunswick
8.6 out of 10, Excellent, (13 reviews)
"Clean convenient location and quiet with comfortable beds. Just what we needed. "
United States
caralyn g.
The price is AED 735
AED 1,369 total
includes taxes & fees
24 Jun - 25 Jun
2King Bed BR Private Apt Downtown Brunswick
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 AED 1,349
AED 2,823 total
includes taxes & fees
23 Jun - 24 Jun
Pemaquid Escape | Curated Comfort + Hot Tub
Exterior

Charming Sheepscot Overlook Cottage

Charming Sheepscot Overlook Cottage
Edgecomb
10.0 out of 10, Exceptional, (10 reviews)
"Great location, great view, great house, great time"
United States
Carol P.
The price is AED 2,387
AED 4,353 total
includes taxes & fees
30 Jun - 1 Jul
Charming Sheepscot Overlook Cottage
Terrace/patio

Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (38 reviews)
"Great place to stay and pet friendly. "
United States
Kevin M.
The price is AED 331
AED 561 total
includes taxes & fees
23 Jun - 24 Jun
Get in touch with nature.
Exterior

Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (153 reviews)
"Such a fabulous stay. The space was bright, clean, and comfortable, and the special touches made it feel even more welcoming. It was larger than expected, and we loved having a mini fridge and coffee machine, perfect for slow mornings or a little wine and cheese at the end of the day. We’d return in a heartbeat."
Canada
Coral
The price is AED 437
AED 557 total
includes taxes & fees
24 Jun - 25 Jun
Large suite/private bath/private entrance on quiet street near Thomas Bay
Interior

Little Lincoln beautiful home

Little Lincoln beautiful home
Brunswick
9.0 out of 10, Wonderful, (16 reviews)
"The host was very welcoming and responsive when we had a question. We would stay here again when we come back to Brunswick. "
United States
Michael S.
The price is AED 680
AED 1,389 total
includes taxes & fees
5 Jul - 6 Jul
Little Lincoln beautiful home
Property grounds

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is AED 908
AED 1,617 total
includes taxes & fees
23 Jun - 24 Jun
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
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 AED 1,212
AED 2,654 total
includes taxes & fees
25 Jun - 26 Jun
Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home
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 AED 454
AED 575 total
includes taxes & fees
23 Jun - 24 Jun
Captain's Guest Room. Authenticity. Value. Near everything. No fees.
Fridge, microwave, oven, stovetop

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.6 out of 10, Exceptional, (33 reviews)
"Wonderful location. It’s right next to Bowdoin. There is a great coffee shop a block away and a grocery store within easy walking distance. The place was spotless. "
United States
Mike S.
The price is AED 992
AED 1,918 total
includes taxes & fees
23 Jun - 24 Jun
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
2 bedrooms, iron/ironing board, bed sheets

Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (3 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is AED 441
AED 953 total
includes taxes & fees
29 Jun - 30 Jun
Cheerful Cottage with Loft 9
Fridge, microwave, oven, stovetop

Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
East Boothbay
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful place, had everything we needed!"
United States
Kathy H.
The price is AED 1,041
AED 2,204 total
includes taxes & fees
27 Jun - 28 Jun
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
TV

Classic New England 1st Floor 3 BR Downtown Brunswick

Classic New England 1st Floor 3 BR Downtown Brunswick
Brunswick
9.6 out of 10, Exceptional, (9 reviews)
"We had a good time in Brunswick.... great location and jumping off point to explore."
United States
Karin S.
Classic New England 1st Floor 3 BR Downtown Brunswick
Beach nearby

Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage

Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage
Pemaquid Beach
9.8 out of 10, Exceptional, (6 reviews)
"Great beach cottage !"
United States
Gwen M.
The price is AED 566
AED 1,157 total
includes taxes & fees
23 Jun - 24 Jun
Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage
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

8/10 Good
"Room was good, staff helpful, breakfast good"
James 2-night trip
Posted 5 hours ago
Flagship Inn and Suites

Frequently asked questions

Can I find vacation rentals in Southport?

Yes, we offer vacation rentals close to well known sights in Southport, or you can go with a more remote option if you're looking for a relaxing stay. Discover why Southport is known for its waterfront and seaside. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best vacation rentals that Southport has to offer?

Generational Southport Property w/ Private Beach Newly Available for Rent!: This Southport vacation home rental is located on the beach and has a fireplace, a balcony, and laundry facilities to put you at ease in your new surroundings. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Southport?

With 27 Expedia vacation rentals, you're sure to find just the right place for your Southport stay.

What’s there to see and do in Southport?

Cultural attractions include Hendricks Hill Museum, whereas Hendricks Head Beach is a spot to enjoy nature. Southport Memorial Library and Burnt Island Living Lighthouse are a couple of places you'll find in the larger area.

What’s a vacation rental in Southport like?

Vacation rentals are private properties where you can stay for a long or short time in Southport. Vacation rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family trip.