Southport Vacation Rentals

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Vacation Rentals in Southport

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (92)
"Jeff was easy to work with and we had a wonderful stay. Perfect location for Graduation weekend. Very good location and quiet. Would recommend. "
Westport "Gold Coast" across from Southport beach

Stamford Suites

4.0 star property
5.6 out of 10, (49)
"Excellent sleep"
The price is CA $179
CA $206 total
includes taxes & fees
Sep 4 - Sep 5
Stamford Suites

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (65)
"Incredible staff, friendly, helpful. "
The price is CA $244
CA $365 total
includes taxes & fees
Sep 7 - Sep 8
DUNE Fairfield Beach

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
The price is CA $236
CA $447 total
includes taxes & fees
Aug 21 - Aug 22
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
The price is CA $356
CA $410 total
includes taxes & fees
Aug 21 - Aug 22
Guesthouse at Norwalk Inn

Business or Weekend escape

9.2 out of 10, Wonderful, (44)
"Very nice owner with great communication. "
The price is CA $118
CA $203 total
includes taxes & fees
Sep 14 - Sep 15
Business or Weekend escape

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

9.0 out of 10, Wonderful, (7)
"This property is well maintained. Some amenities available that made our stay more enjoyable. My only issue was the amount of noise you could hear throughout the night.but once you're asleep it doesn't matter. "
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (16)
"The covered parking was really helpful on a cold day."
Luxury Apartments by Hyatus at The Asher

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

9.4 out of 10, Exceptional, (20)
"Had a great stay!"
The price is CA $204
CA $579 total
includes taxes & fees
Sep 1 - Sep 2
Luxury Designer 2 bedroom+office/3bed vacation home.

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very good, (12)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

10.0 out of 10, Exceptional, (1)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
The price is CA $193
CA $319 total
includes taxes & fees
Aug 23 - Aug 24
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow

9.0 out of 10, Wonderful, (7)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow

Modern House in Black Rock

2.0 star property
9.0 out of 10, Wonderful, (6)
"Very easy stay and great location convenient to Fairfield University . Plenty of options to walk to for coffee or meals. Had everything we needed. Clean, well equipped. Great communication with owners. "
Modern House in Black Rock

Centric property close to all the great things in the city

7.6 out of 10, Good, (12)
"This rental was great accommodation"
The price is CA $217
CA $410 total
includes taxes & fees
Aug 25 - Aug 26
Centric property close to all the great things in the city

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (5)
The price is CA $551
CA $992 total
includes taxes & fees
Aug 22 - Aug 23
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (63)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries

1856 Trading House close to water

9.4 out of 10, Exceptional, (17)
"Close to port Jefferson!"
1856 Trading House close to water

Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

10.0 out of 10, Exceptional, (1)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
The price is CA $994
CA $1,908 total
includes taxes & fees
Aug 22 - Aug 23
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

Modern Beach Home - Waterview, close to restaurants, universities and hospitals

Modern Beach Home - Waterview, close to restaurants, universities and hospitals

Charming 3-bedroom Beach House

Charming 3-bedroom Beach House
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

Frequently asked questions

Can I find a vacation rental in Southport?

Yes, we have vacation rentals near well known attractions in Southport, or you can select a more remote option if you'd like a relaxing place to stay. Our travelers 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 vacation home rentals that Southport has to offer?

Business or Weekend escape: This vacation home rental outside of Southport is equipped with a barbecue grill, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave, and a coffee maker.

How many vacation rentals will I find in Southport?

With 5 Expedia vacation rentals, you're sure 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 larger area, you’ll find South Pine Creek Beach and Fairfield Theater Company.

What are vacation rentals like in Southport?

Vacation rentals are private accommodations you can reserve for a short or long stay in Southport. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for small groups.