Language and Currency

Select your language and currency preferences for the site. Please note that all transactions will be processed in USD

Calendar View
  • Dates
    Any
  • Occupancy
    Any
    - +
    - +
    - +
  • Rooms
    Any
  • Price Range
    Any
  • Amenities
    Any
  • List
  • Map
  • Calendar

Southport Vacation Rentals

1 - 34 of 34 rentals
  PrevNext  
Tue 19 Jun Wed 20 Jun Thu 21 Jun Fri 22 Jun Sat 23 Jun Sun 24 Jun Mon 25 Jun Tue 26 Jun Wed 27 Jun Thu 28 Jun Fri 29 Jun Sat 30 Jun Sun 1 Jul Mon 2 Jul Tue 3 Jul Wed 4 Jul Thu 5 Jul
Frosty Glen, a Southport Island Retreat - Southport, ME Vacation Rental
- 237 249 283 - - - - - - - 429 505 505 505 479 -
Rockhaven Bay Bliss - West Bath, ME Vacation Rental

Rockhaven Bay Bliss

West Bath, ME
4 Bed 1 Bath Sleeps 9
- - - - - - - - - - - 276 353 359 352 343 330
Maine Stay - Boothbay, ME Vacation Rental

Maine Stay

Boothbay, ME
4 Bed 2 Bath Sleeps 12
- - - - - - - - - - - - - - - - -
On The Edgecomb - Edgecomb, ME Vacation Rental

On The Edgecomb

Edgecomb, ME
3 Bed 3 Bath Sleeps 6
- - - - - - 170 209 193 - - - 222 235 217 - -
Casa Dianne II - Boothbay Harbor, ME Vacation Rental

Casa Dianne II

Boothbay Harbor, ME
4 Bed 2 Bath Sleeps 6
- - - 217 231 240 241 241 238 238 289 314 355 357 348 338 345
Barrett's Watch Cottage and Retreat - Boothbay Harbor, ME Vacation Rental
- - - - - 177 - - - 177 - - - - - - -
Damariscotta Lakefront Retreat - Newcastle, ME Vacation Rental
- - 160 185 - - - - - - - - 301 282 - - -
Bufflehead Cove  - Boothbay, ME Vacation Rental

Bufflehead Cove

Boothbay, ME
3 Bed 2.5 Bath Sleeps 7
- - - - - - - 325 314 - - - - - - - -
Peg's Pond House - Trevett, ME Vacation Rental

Peg's Pond House

Trevett, ME
3 Bed 2 Bath Sleeps 7
191 189 188 189 193 216 - - - - - - - 212 227 216 -
Lupine Lane - Boothbay Harbor, ME Vacation Rental

Lupine Lane

Boothbay Harbor, ME
3 Bed 3 Bath Sleeps 8
158 156 158 186 190 193 190 192 196 193 235 260 287 287 288 287 274
Midcoast Serenity - Waldoboro, ME Vacation Rental

Midcoast Serenity

Waldoboro, ME
3 Bed 2 Bath Sleeps 6
102 - - - - - 137 153 154 154 155 166 - - - - -
Eagles View - Bowdoinham, ME Vacation Rental

Eagles View

Bowdoinham, ME
2 Bed 1 Bath Sleeps 6
- - - - - 152 130 163 149 - - - - - - - -
Seaside Bungalow - Boothbay Harbor, ME Vacation Rental

Seaside Bungalow

Boothbay Harbor, ME
2 Bed 1.5 Bath Sleeps 4
- - 104 112 - - - - - - 139 - - - - - -
Cape McKay - Boothbay Harbor, ME Vacation Rental

Cape McKay

Boothbay Harbor, ME
3 Bed 1 Bath Sleeps 5 (4 Adults Max)
- - - - - - - - - - - - - 178 - - -
The Dome House - Boothbay, ME Vacation Rental

The Dome House

Boothbay, ME
2 Bed 1 Bath Sleeps 4
- - 124 221 221 173 - - - - 222 226 - - 169 - -
Linekin Bay Retreat at Wall Point - Boothbay Harbor, ME Vacation Rental
250 250 250 250 250 250 250 250 250 250 - - 285 285 285 - -
The Captain's Cottage - Boothbay Harbor, ME Vacation Rental

The Captain's Cottage

Boothbay Harbor, ME
3 Bed 1.5 Bath Sleeps 5
- - - - 165 192 - - - 190 209 - - - - - -
The Eagle's Nest - Waldoboro, ME Vacation Rental

The Eagle's Nest

Waldoboro, ME
3 Bed 2.5 Bath Sleeps 6
- - - - - - 284 299 - - - - - 367 - - -
The 1909 Cottage - Boothbay Harbor, ME Vacation Rental

The 1909 Cottage

Boothbay Harbor, ME
7 Bed 1.5 Bath Sleeps 14
- - - - - 300 300 300 300 300 - - - - - - -
The Beach House at Wall Point - Boothbay Harbor, ME Vacation Rental
- - - - - - - - - - - 250 - - - - -
River View - Edgecomb, ME Vacation Rental

River View

Edgecomb, ME
3 Bed 2.5 Bath Sleeps 6
250 250 250 250 262 250 250 251 250 250 299 299 272 - - - 264
The Atlantic House at Ocean Point - East Boothbay, ME Vacation Rental
- - - - - - - - - - - - - - - - -
Harpswell Bay House - Harpswell, ME Vacation Rental

Harpswell Bay House

Harpswell, ME
3 Bed 1 Bath Sleeps 6
- - 163 168 - - - - - - - 244 313 319 312 289 -
Drifting In - Harpswell, ME Vacation Rental

Drifting In

Harpswell, ME
2 Bed 1 Bath Sleeps 4
- 140 140 - - 140 140 140 140 140 140 144 160 163 155 - -
Linekin Bay Lookout  - East Boothbay, ME Vacation Rental
- - 148 188 193 235 211 217 - - - - - - - - -
Sunshine Cottage - East Boothbay, ME Vacation Rental

Sunshine Cottage

East Boothbay, ME
2 Bed 2.5 Bath Sleeps 6
- - - 111 119 140 129 137 136 136 127 - - - - - -
Popham Oceanfront Cottage - Popham Beach, ME Vacation Rental
- - - - - - - - - - - - - - - - -
Robinhood Retreat at Georgetown - Georgetown, ME Vacation Rental
- - - - - - - - - - - - - - - - -
Popham Pines Beach Retreat - Phippsburg, ME Vacation Rental
- - 151 - - - - - 192 - - - - - - - -
Cabin on the Shore - East Boothbay, ME Vacation Rental

Cabin on the Shore

East Boothbay, ME
2 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Muirgen Enchantment by the Sea - Boothbay, ME Vacation Rental
- - - - - - - - - - - - - - - - -
Sebasco Serenity - Phippsburg, ME Vacation Rental

Sebasco Serenity

Phippsburg, ME
1 Bed 1 Bath Sleeps 3
- - - - - - - - - - - - - - - - -
The Notebook - Boothbay Harbor, ME Vacation Rental

The Notebook

Boothbay Harbor, ME
4 Bed 2.5 Bath Sleeps 7
- - - - - - - - - - - - - - - - -
Hodge Podge Lodge - Boothbay Harbor, ME Vacation Rental

Hodge Podge Lodge

Boothbay Harbor, ME
3 Bed 3 Bath Sleeps 6
- - - - - - - - - - - - - - - - -

About Southport

Much like the rest of coastal Lincoln County, Southport, Maine affords guests scenic vistas, tranquil neighborhoods, and a rugged coastline nonpareil. Settled by Europeans in 1623 and once called Cape Newagen Island, Southport incorporates the tiny villages of Southport, West Southport, Cape Newagen, and Squirrel island.

Today it has less than 1,000 year-round residents, making our Southport, Maine vacation rentals a choice spot for solitude seekers. Nature lovers flock here for the bountiful grasslands and bird- and whale-watching sites. Lighthouse aficionados head here to admire two restored lights. Hikers come every summer and fall to traverse the 12 acres of peaceful tree-covered terrain near the ocean. It's Maine like it should be seen.

Things to Do in Southport

Like its bigger sisters to the north - Boothbay, Boothbay Harbor, and East Boothbay - Southport boats myriad natural wonders. First-time visitors should hike the 12-acre, half-mile loop of the Hendricks Head Trail - operated by the Boothbay Land Trust - an easy hike, but one that has a few steep and slippery climbs. End the hike at the Hendricks Head Lighthouse at the mouth of the Sheepscot River. Originally constructed in 1829, the 40-foot brick lighthouse and the two-story cottage adjacent are the keepers of spooky tales, such as the infamous "Ghostlady of the Dark" who is said to wander the grounds late at night.

Cuckolds Lighthouse, built in 1892, sits on the opposite end of the island on a separate outcropping and boasts a short tower and a small inn. The Hendricks Hill Museum along the main thoroughfare features artifacts from the ancestors of current island residents as well pictures and navigational instruments.

Day Trips from Southport, Maine

Lincoln County offers abundant natural wonder in towns inside its environs. From Southport it's just a short drive north to other scenic towns in the Boothbay region such as fun-filled Boothbay Harbor, the garden paradise of Boothbay, and quaint East Boothbay. Nearby Nobleboro offers lakefront living at its finest, while Bar Harbor boasts the Acadia National Park and other scenic land.

Quiet and truly charming, Southport, Maine, is the perfect spot to relax and recharge. After staying at one of our Southport, Maine vacation rentals, you'll do just that.

  • Searching ...
  • 34 of 34
No results in this area. Move map or change filters for more rentals.
  • More Map
  • Less Map
Search Here