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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Our top choices for Southport vacation rentals

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 CA $637
CA $959 total
includes taxes & fees
Jul 24 - Jul 25
Award Winning Luxury Carriage House a short stroll from town!

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 CA $517
CA $935 total
includes taxes & fees
Jul 6 - Jul 7
Vacation Creation Downtown Brunswick 2King Beds

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 CA $417
CA $673 total
includes taxes & fees
Jun 28 - Jun 29
Centerview cottage

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 CA $181
CA $466 total
includes taxes & fees
Jul 16 - Jul 17
1 Mi to Maine Street! Mcm-style Home in Brunswick

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, (49 reviews)
"Excellent, clean property. "
United States
Andy H.
The price is CA $401
CA $849 total
includes taxes & fees
Jun 26 - Jun 27
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

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 CA $236
CA $448 total
includes taxes & fees
Jul 10 - Jul 11
Cheerful Cottage Close to Everything 13

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 CA $283
CA $528 total
includes taxes & fees
Jun 24 - Jun 25
2King Bed BR Private Apt Downtown Brunswick

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 CA $501
CA $1,049 total
includes taxes & fees
Jun 24 - Jun 25
Pemaquid Escape | Curated Comfort + Hot Tub

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 CA $920
CA $1,677 total
includes taxes & fees
Jun 30 - Jul 1
Charming Sheepscot Overlook Cottage

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 CA $127
CA $216 total
includes taxes & fees
Jun 24 - Jun 25
Get in touch with nature.

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 CA $173
CA $220 total
includes taxes & fees
Jun 28 - Jun 29
Large suite/private bath/private entrance on quiet street near Thomas Bay

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 CA $262
CA $538 total
includes taxes & fees
Jul 5 - Jul 6
Little Lincoln beautiful home

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

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is CA $352
CA $623 total
includes taxes & fees
Jun 24 - Jun 25
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

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 CA $389
CA $926 total
includes taxes & fees
Jun 25 - Jun 26
Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home

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 CA $175
CA $221 total
includes taxes & fees
Jun 28 - Jun 29
Captain's Guest Room. Authenticity. Value. Near everything. No fees.

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 CA $389
CA $747 total
includes taxes & fees
Jun 28 - Jun 29
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

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 CA $167
CA $363 total
includes taxes & fees
Jun 29 - Jun 30
Cheerful Cottage with Loft 9

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 CA $401
CA $849 total
includes taxes & fees
Jun 27 - Jun 28
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

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

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 CA $210
CA $437 total
includes taxes & fees
Jul 1 - Jul 2
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

Find out more about Southport

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Southport. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.