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

Southport Vacation Rentals

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Check prices for these dates

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

Our top choices for Southport vacation rentals

Classic Suite | Iron/ironing board, WiFi (free), bed sheets

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is ￥27,256
￥40,714 total
includes taxes & fees
Sep 16 - Sep 17
DUNE Fairfield Beach
Standard Room, 1 King Bed, Main Building | Property entrance

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 ￥33,305
￥38,300 total
includes taxes & fees
Sep 15 - Sep 16
Guesthouse at Norwalk Inn
1 bedroom, desk, iron/ironing board, WiFi (free)

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

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (17 reviews)
"The accommodations were incredible. The host provided many helpful materials that made the stay very comfortable. The apartment was very cute and had nice amenities for the guests that go above any beyond what a hotel can provide."
United States
Bailey
The price is ￥21,505
￥35,330 total
includes taxes & fees
Sep 18 - Sep 19
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
1 bedroom, desk, WiFi, bed sheets

4. 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 ￥20,123
￥38,810 total
includes taxes & fees
Sep 15 - Sep 16
Spacious Studio with Pool Table
Interior

5. 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, (27 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveler
The price is ￥18,018
￥58,356 total
includes taxes & fees
Sep 15 - Sep 16
Luxury Designer 2 bedroom+office/3bed vacation home.
Coffee/tea maker, fridge, microwave, oven

6. 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)
"Place was very clean . Communication between owner and us was excellent."
United States
gail s.
The price is ￥33,456
￥89,427 total
includes taxes & fees
Sep 16 - Sep 17
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Beach nearby, sun loungers, beach towels

7. 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 ￥39,017
￥97,204 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Terrace/patio

8. Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (2 reviews)
"Host was attentive and the space was comfortable and exactly what we needed"
United States
Parker M.
The price is ￥22,849
￥53,158 total
includes taxes & fees
Sep 21 - Sep 22
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Coffee/tea maker, fridge, microwave, oven

9. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (5 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
The price is ￥23,011
￥54,228 total
includes taxes & fees
Oct 5 - Oct 6
Modern 2 Bed in BlackRock
1 bedroom, iron/ironing board, WiFi, bed sheets

10. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is ￥47,281
￥73,229 total
includes taxes & fees
Sep 15 - Sep 16
Cozy 1-bedroom house in welcoming Bridgeport
Smart TV

11. 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 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is ￥24,194
￥40,804 total
includes taxes & fees
Sep 15 - Sep 16
Centric property close to all the great things in the city
Fridge, microwave, stovetop, cookware/dishes/utensils

12. 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 ￥20,737
￥45,238 total
includes taxes & fees
Sep 15 - Sep 16
Zen, Spacious & Comfy 2 bed, Lux beds
House (4 Bedrooms) | Interior

13. 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 ￥70,046
￥115,129 total
includes taxes & fees
Sep 16 - Sep 17
4 Mi to Beach & Dtwn! Charming Fairfield Home
Interior

14. 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 ￥58,833
￥111,306 total
includes taxes & fees
Sep 16 - Sep 17
4 Mi to Beach & Dtwn! Charming Fairfield Home
Coffee/tea maker, fridge, microwave, oven

15. Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"We had an awesome time staying Here Everything was super clean And the communication with the host was great we would greatly recommend would definitely stay again!"
United States
Anonymous traveler
The price is ￥20,461
￥50,105 total
includes taxes & fees
Oct 6 - Oct 7
Renovated 2BR Retreat / Modern Comforts Included
Pool

16. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (59 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is ￥13,825
￥23,387 total
includes taxes & fees
Sep 22 - Sep 23
Business or Weekend escape
1 bedroom, desk, iron/ironing board, WiFi (free)

17. Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Downtown Bridgeport
9.4 out of 10, Exceptional, (8 reviews)
"The Orange & Groovy Apt. was as described. All the amenities we needed and we had a lovely time and enjoyed the area. Will book again!"
United States
Betty W.
The price is ￥21,505
￥35,330 total
includes taxes & fees
Sep 15 - Sep 16
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Coffee/tea maker, fridge, microwave, oven

18. 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 ￥32,808
￥69,834 total
includes taxes & fees
Oct 6 - Oct 7
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
Interior

19. 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 ￥16,283
￥27,942 total
includes taxes & fees
Sep 28 - Sep 29
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Coffee/tea maker, fridge, microwave, oven

20. 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 ￥72,074
￥137,186 total
includes taxes & fees
Sep 16 - Sep 17
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

8/10 Good
"Easy check in. Free parking in safe lot. Clean facility. Room was decent. Stayed in better and had rooms with better sound proof walls but overall great pick at price, location and quality. Would stay there again if in the area. Secret hidden gem of the area was KA. WA Korean restaurant. Phenomenal. Hard to get into and would not walk from the hotel because of 95. Maybe during the day with light traffic but not at night busy traffic. But food was amazing."
Kelsey 1-night trip
Posted 7 hours ago
Best Western Executive Hotel Of New Haven - West Haven

Find out more about Southport

Search for holiday rentals in Southport on Expedia! You can easily find your home rentals, villas, holiday apartments in Southport using one of the methods below:

  • View our selection of featured holiday rentals in Southport
  • Use the map to find apartments and other holiday homes in the Southport neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southport while they last

Look no further and take a look at our great range of rental properties in Southport!

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 offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

How many vacation rentals will I find in Southport?

With 4 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 Fairfield Theater Company and Fairfield Beach.

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.