Search 105,200+ Vacation Rentals

Southport 2-bedroom Vacation Rentals, Cabin Rentals & More - 43 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

43 Vacation rentals

Filters applied: 2+ Bedrooms

1 / 17

Newagen House

  • 3
  • 4
  • min stay varies
  • Child friendly

$458.00

Inquire

from $458.00 / night

1 / 27

Southport House

  • 3
  • 6
  • 4 nights min
  • Child friendly
  • Pet friendly

$486.00

Inquire

from $486.00 / night

1 / 21

Southport House

  • 3
  • 6
  • 4 nights min
  • Child friendly
  • Pet friendly

$359.00

Inquire

from $359.00 / night

1 / 17

Newagen House

  • 3
  • 6
  • 4 nights min
  • Child friendly
  • Pet friendly

$283.00

Inquire

from $283.00 / night

1 / 17

Southport House

  • 3
  • 6
  • 4 nights min
  • Child friendly
  • Air conditioning

$193.00

Inquire

from $193.00 / night

1 / 9

Southport House

  • 2
  • 4
  • 14 nights min
  • Ask about children
  • Pet friendly

$165.00

Inquire

from $165.00 / night

1 / 17

Southport House

  • 2
  • 4
  • min stay varies
  • Child friendly
  • Pet friendly

$333.00

Inquire

from $333.00 / night

1 / 24

Southport House

  • 5
  • 10
  • 4 nights min
  • Child friendly
  • Pet friendly

$379.00

Inquire

from $379.00 / night

Your search has been expanded 13.2 miles to include more rentals

(2)

1 / 18

Wiscasset House - 12.7 miles away

  • 4
  • 10
  • 4 nights min
  • Child friendly
  • Pet friendly

$360.00

Excellent (2 reviews)

Inquire

from $360.00 / night

(9)

1 / 16

Georgetown Cottage - 6.3 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
“We can only say that staying here made it one of our best vacations. It lowered my wife's blood by 10 points and everyone hated to leave...”
- Review left on 10/21/2017

$279.00

Excellent (9 reviews)

Inquire

from $279.00 / night

(11)

1 / 12

Harpswell Cottage - 12.6 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 22 mi
  • Child friendly

Responds fast! Avg. 1 hour 59 minutes

“Originally we were just looking for accommodation within easy reach of Brunswick to enable us to visit relatives, but within a very short time we realised we had found so much more. Set in the pines with the tidal bay where we watched seals, sea...”
- Review left on 09/25/2015

$152.00

Excellent (11 reviews)

Book

from $152.00 / night

1 / 19

Boothbay House - 7.6 miles away

  • 2
  • 4
  • 4 nights min
  • Ask about children
  • Pet friendly

$304.00

Inquire

from $304.00 / night

1 / 13

East Boothbay House - 3.5 miles away

  • 4
  • 6
  • min stay varies
  • Child friendly
  • Pet friendly

$285.00

Inquire

from $285.00 / night

1 / 24

Walpole House - 10.4 miles away

  • 3
  • 6
  • 4 nights min
  • Child friendly
  • Air conditioning

$344.00

Inquire

from $344.00 / night

(1)

1 / 20

Boothbay Harbor House - 2.1 miles away

  • 4
  • 7
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$315.00

Very Good (1 reviews)

Inquire

from $315.00 / night

1 / 27

Harpswell House - 13.2 miles away

  • 3
  • 6
  • 4 nights min
  • Child friendly
  • Air conditioning

$354.00

Inquire

from $354.00 / night

(1)

1 / 14

East Boothbay House - 2.7 miles away

  • 3
  • 6
  • 4 nights min
  • Child friendly
  • Pet friendly

$329.00

Excellent (1 reviews)

Inquire

from $329.00 / night

1 / 18

East Boothbay House - 3 miles away

  • 3
  • 8
  • 4 nights min
  • Child friendly

$235.00

Inquire

from $235.00 / night

1 / 24

East Boothbay House - 5 miles away

  • 4
  • 7
  • 4 nights min
  • Child friendly
  • Pet friendly

$344.00

Inquire

from $344.00 / night

(2)

1 / 27

Wiscasset House - 7.6 miles away

  • 2
  • 6
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$311.00

Excellent (2 reviews)

Inquire

from $311.00 / night

(9)

1 / 22

Georgetown House - 5.4 miles away

  • 5
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 3 hours 10 minutes

“The house is stunning, in a very private setting, right on the water, plenty big enough for 8-10 people. Great room is gorgeous with beautiful views of the river. Stone wall in the great room and outside(where you can drink your morning coffee in the...”
- Review left on 09/05/2019

$281.00

Excellent (9 reviews)

Book

from $281.00 / night

1 / 20

East Boothbay House - 3.5 miles away

  • 2
  • 4
  • 4 nights min
  • Child friendly
  • Air conditioning

$332.00

Inquire

from $332.00 / night

(2)

1 / 14

Wiscasset Cottage - 8.6 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 25 mi
  • Child friendly
  • Private garden

$172.00

Excellent (2 reviews)

Book

from $172.00 / night

(9)

1 / 17

Phippsburg Cottage - 10.6 miles away

  • 3
  • 6
  • min stay varies
  • Child friendly
  • Pet friendly
“My wife and I along with our 36 yr old son stayed recently and had a wonderful time. The cottage was fully equipped, comfortable and meticulously clean. Water views and a very short walk to their waterfront. Another short walk or drive to Anna's...”
- Review left on 08/21/2016

$205.00

Very Good (9 reviews)

Book

from $205.00 / night

1 / 19

Georgetown House - 5.3 miles away

  • 2
  • 6
  • 4 nights min
  • Child friendly

$344.00

Inquire

from $344.00 / night

1 / 30

East Boothbay House - 4 miles away

  • 4
  • 7
  • min stay varies
  • Child friendly
  • Pet friendly

$279.00

Inquire

from $279.00 / night

(2)

1 / 20

East Boothbay House - 4 miles away

  • 3
  • 6
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$317.00

Excellent (2 reviews)

Inquire

from $317.00 / night

1 / 27

Boothbay Harbor House - 2.1 miles away

  • 7
  • 11
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

$714.00

Inquire

from $714.00 / night

(3)

1 / 30

Boothbay House - 3.4 miles away

  • 4
  • 10
  • 4 nights min
  • Child friendly
  • Pet friendly

$300.00

Very Good (3 reviews)

Inquire

from $300.00 / night

1 / 22

Boothbay Harbor House - 3.5 miles away

  • 4
  • 8
  • 4 nights min
  • Child friendly
  • Pet friendly

$225.00

Inquire

from $225.00 / night

1 / 12

Boothbay Harbor House - 3 miles away

  • 2
  • 4
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$191.00

Inquire

from $191.00 / night

1 / 20

Squirrel Island House - 3 miles away

  • 4
  • 8
  • 4 nights min
  • Child friendly
  • Pet friendly

$243.00

Inquire

from $243.00 / night

(8)

1 / 16

Round Pond House - 13 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
“If you are looking for the perfect spot and cottage to spend some relaxing days, please , please rent this cottage. The weather was perfect for us to ride our motorcycle. This cottage was supplied with absolutely everything. The sitting area in...”
- Review left on 09/25/2016

$75.00

Excellent (8 reviews)

Inquire

from $75.00 / night

(1)

1 / 25

Boothbay House - 4.8 miles away

  • 2
  • 6
  • 4 nights min
  • Child friendly
  • Pet friendly

$308.00

Excellent (1 reviews)

Inquire

from $308.00 / night

1 / 25

Georgetown House - 2.3 miles away

  • 3
  • 6
  • 4 nights min
  • Ask about children
  • Pet friendly

$344.00

Inquire

from $344.00 / night

1 / 25

Georgetown House - 2.3 miles away

  • 3
  • 6
  • 4 nights min
  • Child friendly

$300.00

Inquire

from $300.00 / night

(3)

1 / 32

Boothbay House - 4.2 miles away

  • 3
  • 6
  • 4 nights min
  • Child friendly
  • Pet friendly

$311.00

Excellent (3 reviews)

Inquire

from $311.00 / night

(1)

1 / 30

East Boothbay House - 4 miles away

  • 8
  • 16
  • 4 nights min
  • Child friendly
  • Pet friendly

$944.00

Excellent (1 reviews)

Inquire

from $944.00 / night

(4)

1 / 32

Boothbay House - 2.9 miles away

  • 5
  • 10
  • 4 nights min
  • Child friendly
  • Pet friendly

$443.00

Very Good (4 reviews)

Inquire

from $443.00 / night

1 / 23

Georgetown House - 5.6 miles away

  • 2
  • 4
  • 4 nights min
  • Child friendly

$344.00

Inquire

from $344.00 / night