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 7 - Jul 8
4 Mi to Beach & Dtwn! Charming Fairfield Home

Elite room stay

Elite room stay
Bridgeport
The price is CA $294
CA $490 total
includes taxes & fees
Jul 7 - Jul 8
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 $272 total
includes taxes & fees
Jul 13 - Jul 14
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 $484
CA $557 total
includes taxes & fees
Jul 7 - Jul 8
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 14 - Jul 15
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 $259
CA $520 total
includes taxes & fees
Jul 7 - Jul 8
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 $1,957 total
includes taxes & fees
Jul 8 - Jul 9
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 $1,087 total
includes taxes & fees
Jul 7 - Jul 8
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 $391
CA $797 total
includes taxes & fees
Jul 8 - Jul 9
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 $278
CA $753 total
includes taxes & fees
Jul 7 - Jul 8
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

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

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.