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

Southport Vacation Rentals

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Our top choices for Southport vacation rentals

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (96 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is CA $268
CA $395 total
includes taxes & fees
Jul 29 - Jul 30
DUNE Fairfield Beach

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is CA $866
CA $1,493 total
includes taxes & fees
Jul 12 - Jul 13
Beechmont - Perfect for Family Retreat!

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 CA $734
CA $1,084 total
includes taxes & fees
Jul 6 - Jul 7
4 Mi to Beach & Dtwn! Charming Fairfield Home

Elite room stay

Elite room stay
Bridgeport
The price is CA $294
CA $486 total
includes taxes & fees
Jul 6 - Jul 7
Elite room stay

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, Exceptional, (16 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is CA $312
CA $587 total
includes taxes & fees
Jul 8 - Jul 9
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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, (13 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
The price is CA $155
CA $275 total
includes taxes & fees
Jul 12 - Jul 13
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Renovated 2 bedroom entire apartment w/parking

Renovated 2 bedroom entire apartment w/parking
Ansonia
10.0 out of 10, Exceptional, (2 reviews)
"Host was very attentive making sure everything was going well, apartment was great would definitely stay again "
United States
Sophia
The price is CA $234
CA $406 total
includes taxes & fees
Jul 12 - Jul 13
Renovated 2 bedroom entire apartment w/parking

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 CA $463
CA $532 total
includes taxes & fees
Jul 6 - Jul 7
Guesthouse at Norwalk Inn

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, Exceptional, (41 reviews)
"The location is beautiful and the hosts very amenable. Everything was clean, tidy and welcoming and there is a beautiful view out one of the bedroom windows to the lake in the back. I can highly recommend this destination and look forward to staying here again on a return trip!"
United States
Anonymous traveller
The price is CA $268
CA $495 total
includes taxes & fees
Jul 19 - Jul 20
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Beach Apartment in Woodmont Milford 102

Beach Apartment in Woodmont Milford 102
Milford
The price is CA $230
CA $482 total
includes taxes & fees
Jul 6 - Jul 7
Beach Apartment in Woodmont Milford 102

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
The price is CA $496
CA $1,100 total
includes taxes & fees
Jul 22 - Jul 23
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

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 CA $1,017
CA $1,922 total
includes taxes & fees
Jul 6 - Jul 7
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
The price is CA $622
CA $1,071 total
includes taxes & fees
Jul 6 - Jul 7
4 Mi to Beach & Dtwn! Charming Fairfield Home

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Excellent home, met all expectations, and attentive staff"
United States
Steve G.
The price is CA $994
CA $1,808 total
includes taxes & fees
Jul 7 - Jul 8
New Beach Home near Stamford Downtown/Shippan

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Cove - East Side - Shippan
8.0 out of 10, Very good, (6 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is CA $312
CA $696 total
includes taxes & fees
Jul 6 - Jul 7
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

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, (37 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is CA $537
CA $1,052 total
includes taxes & fees
Jul 14 - Jul 15
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

The Daydreamer - Walk To Walnut Beach, Restaurant + Shops
Milford
9.6 out of 10, Exceptional, (20 reviews)
"Cute very small house"
United States
Patricia M.
The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is CA $204
CA $596 total
includes taxes & fees
Jul 9 - Jul 10
Modern Luxe 1BR Apt in Downtown Stamford

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
The price is CA $225
CA $686 total
includes taxes & fees
Jul 6 - Jul 7
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

McAngel Haven: 5 mins from Yale

McAngel Haven: 5 mins from Yale
West Haven
9.6 out of 10, Exceptional, (23 reviews)
"Excellent location Clean and spacious Comfortable beds "
United States
Joseph T.
The price is CA $326
CA $753 total
includes taxes & fees
Jul 7 - Jul 8
McAngel Haven: 5 mins from Yale
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

Everything you need to know about Southport vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southport vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southport vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Southport vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southport. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southport vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southport vacation rentals we have selected for you start as low as CA $208 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southport rentals

At Expedia, we put the best Southport vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southport rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southport vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southport. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation home rental outside of Southport is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Discovery Museum, or get out into nature at a spot like Southport Beach. In the larger area, you’ll find Country Club of Fairfield 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.