A Gothic-style church with a tall steeple, large arched windows, and a clock tower.

Holiday Homes in Southport

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Southport holiday homes

A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

1. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fairfield
10.0 out of 10, 18, (18 reviews)
"Place was very clean . Communication between owner and us was excellent."
United States
gail s.
The price is AU$803
includes taxes & fees
16 Sept - 17 Sept
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

2. Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
6.6 out of 10, 17, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is AU$371
includes taxes & fees
17 Sept - 18 Sept
Centric property close to all the great things in the city
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

3. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fairfield
10.0 out of 10, 39, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is AU$841
includes taxes & fees
30 Sept - 1 Oct
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A swimming pool at night with blue lighting.

4. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, 59, (59 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is AU$215
includes taxes & fees
22 Sept - 23 Sept
Business or Weekend escape
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

5. Elite room stay

Elite room stay
Bridgeport
The price is AU$474
includes taxes & fees
17 Sept - 18 Sept
Elite room stay
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

6. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.4 out of 10, 20, (20 reviews)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
The price is AU$1,269
includes taxes & fees
16 Sept - 17 Sept
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

7. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
10.0 out of 10, 1, (1 review)
"Beautiful home! Host was super responsive to questions. The entire house was super clean and welcoming. The bed was comfortable and smelled fresh. There was a personalized welcome sign that was a nice touch and some (much needed) snacks after our almost 3 hour drive. Expectations were well within reason and easily manageable. I would 100% rent again."
United States
Raelyn O.
The price is AU$1,053
includes taxes & fees
16 Sept - 17 Sept
4 Mi to Beach & Dtwn! Charming Fairfield Home
A bedroom with two beds, a nightstand with a lamp, a framed picture on the wall, and a window with curtains.

8. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is AU$585
includes taxes & fees
29 Sept - 30 Sept
Gilded Age Luxury Surrounded by Nature
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

9. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, 15, (15 reviews)
"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."
United States
Melissa H.
The price is AU$973
includes taxes & fees
16 Sept - 17 Sept
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A bedroom with two beds, a wooden dresser, and a mirror.

10. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is AU$655
includes taxes & fees
18 Sept - 19 Sept
Cozy 1-bedroom house in welcoming Bridgeport
A two-story house with a porch, stone steps, and a variety of plants.

11. Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
8.8 out of 10, 10, (10 reviews)
"Plenty of bedrooms and space for the family. Very prompt communication with host."
United States
David K.
The price is AU$1,691
includes taxes & fees
16 Sept - 17 Sept
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

12. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is AU$2,089
includes taxes & fees
17 Sept - 18 Sept
Beechmont - Perfect for Family Retreat!
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

13. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, 19, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is AU$531
includes taxes & fees
20 Sept - 21 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A modern kitchen with white cabinets, a marble island, and black bar stools.

14. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
10.0 out of 10, 2, (2 reviews)
"A great location. We were less than 15 minutes from everything we did. House was a super layout for our large group."
United States
Mark F.
The price is AU$1,055
includes taxes & fees
16 Sept - 17 Sept
Spacious Retreat with Game Room and Fire Pit
A campfire with a wooden table and benches by a lake.

15. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, 42, (42 reviews)
"Nice stay"
United States
Christopher J.
The price is AU$478
includes taxes & fees
4 Oct - 5 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

16. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
9.4 out of 10, 3, (3 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is AU$1,076
includes taxes & fees
17 Sept - 18 Sept
Renovated Retreat with Heated Pool
A modern kitchen with granite countertops, a dining area with black chairs, a living room with a sofa and a coffee table, and a large window with a view.

17. 5BR Beach House, Water Views, Game Room, Backyard

5BR Beach House, Water Views, Game Room, Backyard
Cove - East Side - Shippan
9.4 out of 10, 31, (31 reviews)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
The price is AU$1,217
includes taxes & fees
21 Sept - 22 Sept
5BR Beach House, Water Views, Game Room, Backyard
A living room with a sofa set, a coffee table, and a television on a stand.

18. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking
Cove - East Side - Shippan
8.6 out of 10, 9, (9 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is AU$835
includes taxes & fees
20 Sept - 21 Sept
Spacious Stamford Home | Family, Work, Parking

19. 5BR Beach House, Game Room + Huge Backyard

5BR Beach House, Game Room + Huge Backyard
Cove - East Side - Shippan
10.0 out of 10, 26, (26 reviews)
"Great stay!"
United States
Kyra S.
The price is AU$1,546
includes taxes & fees
16 Sept - 17 Sept
5BR Beach House, Game Room + Huge Backyard
A wooden deck with chairs and a kayak, leading to a beach with a view of the ocean.

20. Shore to Shore Coastal Retreat at Asharoken

Shore to Shore Coastal Retreat at Asharoken
Northport
10.0 out of 10, 1, (1 review)
"We had a great time at this Vrbo. The house is spacious and the backyard absolutely beautiful. We brought two babies under 2 and it was a perfect spot. The private beach is just steps away and lovely for low-key beach days. The fridge was not working properly, and Joe let us know ahead of time and provided us with a mini fridge that worked, which made everything easy. He also ordered us more paper towels and dish soap while we were there which was super helpful and accomodating. Would absolutely...
United States
Rachel W.
The price is AU$1,538
includes taxes & fees
16 Sept - 17 Sept
Shore to Shore Coastal Retreat at Asharoken
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

Red Carpet Inn

Red Carpet Inn

10/10 Excellent
"The room was clean and the bed was a nice king size bed. Staff was very friendly and easy to deal with. Parking was free and convenient."
Eliot 1-night trip
Posted 2 hours ago
Red Carpet Inn

Find out more about Southport

Southport Holiday Homes information

Number of reviews
269
Accommodation
248 Holiday Homes
Lowest Price
AU$215
Highest Price
AU$2,089

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