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

Southport Holiday Rentals

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Our top choices for Southport holiday rentals

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (111 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is NZ$441
includes taxes & fees
13 Sept - 14 Sept
DUNE Fairfield Beach

2. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is NZ$419
includes taxes & fees
27 Aug - 28 Aug
Guesthouse at Norwalk Inn

3. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is NZ$1,254
includes taxes & fees
9 Sept - 10 Sept
4 Mi to Beach & Dtwn! Charming Fairfield Home

4. 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, Exceptional, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is NZ$1,039
includes taxes & fees
21 Sept - 22 Sept
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

5. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is NZ$2,506
includes taxes & fees
30 Aug - 31 Aug
Beechmont - Perfect for Family Retreat!

6. Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
9.6 out of 10, Exceptional, (12 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
The price is NZ$331
includes taxes & fees
15 Sept - 16 Sept
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

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

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
10.0 out of 10, Exceptional, (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 NZ$1,251
includes taxes & fees
7 Sept - 8 Sept
4 Mi to Beach & Dtwn! Charming Fairfield Home

8. 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, Exceptional, (18 reviews)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is NZ$1,060
includes taxes & fees
16 Sept - 17 Sept
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

9. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is NZ$797
includes taxes & fees
6 Sept - 7 Sept
Cozy 1-bedroom house in welcoming Bridgeport

10. 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
6.8 out of 10, (16 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
The price is NZ$446
includes taxes & fees
27 Aug - 28 Aug
Centric property close to all the great things in the city

11. 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, Exceptional, (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 NZ$1,404
includes taxes & fees
8 Sept - 9 Sept
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

12. Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is NZ$448
includes taxes & fees
27 Aug - 28 Aug
Spacious Studio with Pool Table

13. Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
10.0 out of 10, Exceptional, (2 reviews)
"A wonderful place. Beds where comfortable. Would most definitely come back there again. Quiet and safe atmosphere. Not far from the highway. Host was very nice."
United States
Lisa J.
The price is NZ$494
includes taxes & fees
31 Aug - 1 Sept
Zen, Spacious & Comfy 2 bed, Lux beds

14. 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, Excellent, (10 reviews)
"Plenty of bedrooms and space for the family. Very prompt communication with host."
United States
David K.
The price is NZ$2,094
includes taxes & fees
21 Sept - 22 Sept
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

15. Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.6 out of 10, Exceptional, (26 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveller
The price is NZ$679
includes taxes & fees
21 Sept - 22 Sept
Luxury Designer 2 bedroom+office/3bed vacation home.

16. Nama-stay, sweet pink Saugatuck Shores beach cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.2 out of 10, Wonderful, (17 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
The price is NZ$1,221
includes taxes & fees
23 Sept - 24 Sept
Nama-stay, sweet pink Saugatuck Shores beach cottage

17. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (5 reviews)
"Cozy get away"
United States
Anonymous traveller
The price is NZ$548
includes taxes & fees
27 Aug - 28 Aug
Modern 2 Bed in BlackRock

18. King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great "
United States
Ricky W.
The price is NZ$587
includes taxes & fees
27 Aug - 28 Aug
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

19. Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"Nice place to stay "
United States
Maria Elena G.
The price is NZ$778
includes taxes & fees
21 Sept - 22 Sept
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Southport holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Southport. 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 Southport. 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 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 holiday 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 Southport short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Southport?

Yes, there are holiday rentals close to the most popular sights in Southport, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Southport has a good selection of restaurants. Make sure you have time to check out the hockey games and beaches during your trip.

What are some of the best holiday rentals that Southport has to offer?

Charming Home in Seaside: This holiday home rental outside of Southport is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Southport?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Southport stay.

What can I see and do in Southport?

Explore the area and family-friendly sights such as Norwalk Maritime Aquarium, or get out into nature at a spot like Southport Beach. In the wider area, you’ll find Fairfield Theater Company and Fairfield Beach.

What are holiday rentals like in Southport?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Southport. Holiday rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.