Southport vacation rentals

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Top-rated vacation rentals in Southport

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in South Bristol

4.98 out of 5 average rating, 344 reviews

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Dec 27 – Jan 3

G$32,211 GYD per night

Guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 430 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, comfy, spacious, colorful and bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Two spectacular state parks with expansive beaches within a scenic 35 minute drive! Just 45 minutes (33 miles) to Coastal Maine Botanical Gardens! Saturday check-in may be available before mid June. Please message us.

May 7 – 14

G$27,948 GYD per night

Guest favorite

Guest suite in Woolwich

4.92 out of 5 average rating, 187 reviews

Private Guest Apartment with separate entrance.

Your perfect base for discovering all the wonderful places Midcoast Maine has to offer. Located on a peaceful wooded lot, this one bedroom apartment sits on the ground floor of our 2-story home. Separate private deck entry with parking, comfortable queen bedroom, Wifi; fully equipped kitchenette; spacious bathroom with large jacuzzi tub and separate walk-in shower. Roomy sitting/dining area opens out onto deck with Adirondack chairs; table and grill. Large smart TV. Fast Wi-Fi. Firepit.

May 27 – Jun 3

G$19,507 GYD per night

Guest favorite

Cottage in Boothbay Harbor

4.98 out of 5 average rating, 327 reviews

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

Dec 12 – 19

G$34,251 GYD per night

Guest favorite

Treehouse in Georgetown

4.98 out of 5 average rating, 402 reviews

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

Dec 14 – 21

G$70,591 GYD per night

Guest favorite

Guesthouse in Georgetown

4.9 out of 5 average rating, 136 reviews

Island Alchemy Cottage

Charming cottage on a beautiful island near marina, beaches, restaurants, and hiking trails. Wonderful mid-coast Maine location for lots of possibilities for outdoor adventures, antiquing, visiting art galleries and shops, and enjoying delicious cuisine. The cottage has everything you need for a peaceful getaway. Decorated with natural elements and local art pieces to get you in the mood for this beautiful location.

Aug 4 – 11

G$25,963 GYD per night

Guest favorite

Guesthouse in Boothbay Harbor

5.0 out of 5 average rating, 225 reviews

The Sparrow’s Nest Charming Country Cottage

The Sparrow's Nest is on a quiet country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful and peaceful country surroundings, gardens, and the miracle of nature. What a delight to wake up to the sound of birdsong while enjoying a cup of local coffee, or sitting by the outdoor fire sipping wine and marveling at the night sky.

Oct 14 – 21

G$90,064 GYD per night

Guest favorite

Cabin in Boothbay Harbor

4.96 out of 5 average rating, 193 reviews

Lakeside 3 BR Cabin in Boothbay Harbor

This swanky mid-60's cabin sits on a hill overlooking West Harbor pond in the town of Boothbay Harbor. It offers privacy yet is close to everything downtown Boothbay Harbor has to offer. It is great for couples, solo adventurers, business travelers and families (with kids), and large enough to accommodate bigger groups. If you would like to bring along your canine pal feel free, they are welcome (sorry no cats).

Oct 20 – 27

G$41,241 GYD per night

Superhost

Apartment in Boothbay Harbor

4.79 out of 5 average rating, 134 reviews

Beautiful Studio in downtown Boothbay Harbor

Beautiful, Large, first floor studio in downtown Boothbay Harbor. 4 minute walk to the harbor, footbridge, shops and restaurants. Located behind the Opera House. 1 queen Bed and 2 twins. Perfect for a family. Fully furnished. Two beautiful, big, bay windows, spacious and homie. Full kitchen with all pots pans and liens available. WiFi T.V. Free off street Parking for one car across the street.

Oct 17 – 24

G$29,443 GYD per night

Guest favorite

Guest suite in Freeport

4.95 out of 5 average rating, 197 reviews

Weather's Edge, Freeport

Come enjoy the historic charm of South Freeport. This antique home and cozy accommodation await you, featuring a private entrance, private room, private full bath, t.v. with cable, and wi-fi. This is a second-floor room, accessed from a dramatic original (steep) staircase, and is conveniently located in an area of lovely homes, with Freeport Village just five minutes away.

May 18 – 25

G$14,515 GYD per night

Guest favorite

Home in Lisbon

4.94 out of 5 average rating, 331 reviews

Unplug at a Beachy Bolthole with Classic New England Style

Chill on the porch after exploring a scenic local walking trail and soak up the serenity of this breezy blue and white hideaway. Striped oars, starfish, smooth shells, and ocean scenes blend with shades of teal and aqua for a thoroughly calm space. There are EV chargers behind the post office. It’s around a block and a half.

Jan 8 – 15

G$13,794 GYD per night

Guest favorite

Apartment in Boothbay

4.96 out of 5 average rating, 259 reviews

Sunnymeade

Centrally located close to Boothbay Harbor, East Boothbay and Southport Island. Coastal Maine Botanical Gardens, Boothbay Region Land Trust's 26 hiking trails, Boothbay Railroad Village with live steam train rides and much, much more are great spots to visit.

Sep 23 – 30

G$21,248 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Southport vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Southport's top sights

The Spa at Spruce Point Inn3 locals recommend

Robinson's Wharf38 locals recommend

Boathouse Bistro | Tapas Bar & Restaurant30 locals recommend

Newagen Seaside Inn7 locals recommend

Boothbay Lobster Wharf10 locals recommend

Boothbay Harbor Maine Puffin Cruises24 locals recommend

Other great vacation rentals in Southport

Guest favorite

Cabin in Boothbay Harbor

4.87 out of 5 average rating, 108 reviews

Sebasco Sprucewold Cabin@ the Beach

Oct 5 – 12

G$35,854 GYD per night

Guest favorite

Apartment in Edgecomb

4.91 out of 5 average rating, 297 reviews

Sunny Apt in Woods 10 Min to 3 Towns- Dog Friendly

Oct 29 – Nov 5

G$21,132 GYD per night

Guest favorite

Cabin in Bremen

4.95 out of 5 average rating, 173 reviews

Ocean Front Cottage: Little Heaven

Sep 5 – 12

G$33,034 GYD per night

Guest favorite

Apartment in Damariscotta

4.92 out of 5 average rating, 254 reviews

Fernald's Backside

Nov 22 – 29

G$24,471 GYD per night

Guest favorite

Guest suite in Georgetown

4.97 out of 5 average rating, 322 reviews

Luxury suite, fireplace, jacuzzi

Oct 16 – 23

G$45,424 GYD per night

Guest favorite

Cottage in Edgecomb

4.91 out of 5 average rating, 106 reviews

Spectacular Water View Cottage

Nov 5 – 12

G$26,554 GYD per night

Guest favorite

Cottage in Topsham

4.95 out of 5 average rating, 212 reviews

Cozy waterfront home on Merrymeeting Bay.

Oct 22 – 29

G$33,510 GYD per night

Guest favorite

Apartment in Boothbay Harbor

5.0 out of 5 average rating, 60 reviews

Harbor for Two

Oct 28 – Nov 4

G$28,711 GYD per night

Show all

Other great vacation rentals in Southport

Guest favorite

Home in Southport

4.97 out of 5 average rating, 30 reviews

Decker Cove Southport Island Paradise

May 25 – Jun 1

G$107,015 GYD per night

Guest favorite

Apartment in Bath

4.97 out of 5 average rating, 33 reviews

1820s Maine Cottage with Garden

Aug 13 – 20

G$27,367 GYD per night

Guest favorite

Home in Georgetown

5.0 out of 5 average rating, 22 reviews

Moss House: Modern Waterfront Cabin in the Woods.

Sep 23 – 30

G$121,733 GYD per night

Guest favorite

Apartment in Wiscasset

5.0 out of 5 average rating, 41 reviews

Bright apt on quiet Westport Isle with river view

Dec 3 – 10

G$37,599 GYD per night

Guest favorite

Cottage in Georgetown

4.98 out of 5 average rating, 98 reviews

Cottage on Todd Bay

Oct 21 – 28

G$33,823 GYD per night

Guest favorite

Guesthouse in Brunswick

4.95 out of 5 average rating, 91 reviews

Modern Brunswick Cottage near Bowdoin & Downtown

Dec 13 – 20

G$18,511 GYD per night

Guest favorite

Apartment in Woolwich

5.0 out of 5 average rating, 26 reviews

Cozy, MidCoast Apartment

Mar 20 – 27

G$26,759 GYD per night

Guest favorite

Home in Edgecomb

4.93 out of 5 average rating, 43 reviews

Merryhaven- Edgecomb/Boothbay/Damariscotta

May 20 – 27

G$22,530 GYD per night

Show all

Quick stats about vacation rentals in Southport

Total rentals
230 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
140 properties are a good fit for families
Total number of reviews
4.9K reviews
Nightly prices starting at
G$12,506 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Southport?
Yes! Work meets play with ease at over 110 vacation rentals in Southport featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Southport?
Four-legged friends are welcome in Southport. Choose from more than 60 vacation rentals for guests traveling with pets.
Do cottage rentals in Southport have a bbq area?
Absolutely! We offer over 10 cottage rentals with a bbq area in Southport. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Southport?
Experience the best of Southport with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly cabin rentals in Southport?
Southport has more than 10 family-friendly cabin rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do boutique hotel rentals in Southport have wifi?
Absolutely! We offer over 20 boutique hotel rentals with wifi in Southport. Enjoy a tailored experience with all the comforts you desire.
Do boutique hotel rentals in Southport have air conditioning?
Absolutely! We offer over 10 boutique hotel rentals with air conditioning in Southport. Enjoy a tailored experience with all the comforts you desire.
Are there Southport vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Southport, available on Airbnb. Make a splash and soak up the sun in style!

Southport vacation rentals

Top-rated vacation rentals in Southport

Vacation rentals for every style

Houses

Apartments

Cabins

Popular amenities for Southport vacation rentals

Stay near Southport's top sights

Other great vacation rentals in Southport

Cabin in Boothbay Harbor

Apartment in Edgecomb

Cabin in Bremen

Apartment in Damariscotta

Guest suite in Georgetown

Cottage in Edgecomb

Cottage in Topsham

Apartment in Boothbay Harbor

Other great vacation rentals in Southport

Home in Southport

Apartment in Bath

Home in Georgetown

Apartment in Wiscasset

Cottage in Georgetown

Guesthouse in Brunswick

Apartment in Woolwich

Home in Edgecomb

Quick stats about vacation rentals in Southport

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Southport?

Are there pet-friendly vacation rentals in Southport?

Do cottage rentals in Southport have a bbq area?

How much does it cost to stay in house rentals in Southport?

Are there family-friendly cabin rentals in Southport?

Do boutique hotel rentals in Southport have wifi?

Do boutique hotel rentals in Southport have air conditioning?

Are there Southport vacation rentals on Airbnb with pools?

Destinations to explore