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Westport Holiday Rentals

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Our top choices for Westport holiday rentals

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7)
"So cute and comfortable "
United States
Maria
The price is AU$422
includes taxes & fees
12 Dec - 13 Dec
Spacious Studio with Pool Table

The Mansion Hotel-style

The Mansion Hotel-style
2.5 star property
Norwalk
8.6 out of 10, Excellent, (19)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is AU$152
includes taxes & fees
12 Dec - 13 Dec
The Mansion Hotel-style

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield
9.0 out of 10, Wonderful, (77)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is AU$439
includes taxes & fees
14 Dec - 15 Dec
Renovated 2BR Retreat / Modern Comforts Included

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
10.0 out of 10, Exceptional, (2)
"Ricardo’s place was perfect for our needs! A small, clean and cozy place, not far from our daytime destination, the apartment offers all the basics - kitchenette, nice bathroom and modern shower, a comfy Queen Size bed, and even some snacks and essentials for a comfortable stay. The area has some restraunts and bars nearby too, though we were happy to stay in and watch some Netflix. I would highly recommend this apartment to a friend, and Ricardo has been a pleasure. Thanks so much!"
United States
Anonymous traveller
The price is AU$248
includes taxes & fees
17 Dec - 18 Dec
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Shelton
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is AU$295
includes taxes & fees
17 Dec - 18 Dec
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

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

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Fairfield
10.0 out of 10, Exceptional, (1)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
The price is AU$479
includes taxes & fees
17 Dec - 18 Dec
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

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

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Greenwich
9.6 out of 10, Exceptional, (23)
"The property was beautiful and clean, very comfortable with a nice view of the lake! Our hosts were helpful and attentive without being intrusive in any way. Our stay was peaceful and restful, just perfect. "
United States
Victoria R.
The price is AU$405
includes taxes & fees
15 Dec - 16 Dec
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
2.0 star property
Kings Park
10.0 out of 10, Exceptional, (13)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
The price is AU$271
includes taxes & fees
22 Dec - 23 Dec
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Newly renovated Private bedroom near Stony Brook University

Newly renovated Private bedroom near Stony Brook University
2.0 star property
Stony Brook
8.0 out of 10, Very good, (2)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
Newly renovated Private bedroom near Stony Brook University

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is AU$224
includes taxes & fees
1 Jan - 2 Jan 2026
Business or Weekend escape

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is AU$369
includes taxes & fees
24 Dec - 25 Dec
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Brooklawn - St. Vincent
8.0 out of 10, Very good, (1)
"It was clean "
United States
Burton
The price is AU$437
includes taxes & fees
4 Jan - 5 Jan 2026
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The ARLO - Walk to Brewery and Restaurants

The ARLO - Walk to Brewery and Restaurants
Milford
9.4 out of 10, Exceptional, (3)
"Very nice house....loved the front enclosed porch, and the kitchen was amazing with everything we needed. The deck with the Blackstone Grill was a great place to sit and relax. We enjoyed many of the nearby restaurants too. Matt and Jess were great hosts!J&J, Mooresville, NC"
United States
Jena
The price is AU$555
includes taxes & fees
21 Dec - 22 Dec
The ARLO - Walk to Brewery and Restaurants

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

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (22)
"Beautifully appointed luxury 2 nd floor accommodations in the city of Bridgeport. Guests could comfortably stay for multiple nights with the well equipped kitchen and dining room space. "
United States
Tessa P.
The price is AU$678
includes taxes & fees
12 Dec - 13 Dec
Luxury Designer 2 bedroom+office/3bed vacation home.

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Fairfield
10.0 out of 10, Exceptional, (22)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is AU$762
includes taxes & fees
7 Jan - 8 Jan 2026
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (73)
"Location was perfect!"
United States
Linda J P.
The price is AU$930
includes taxes & fees
4 Jan - 5 Jan 2026
Captain's Cottage - Cold Spring Harbor Water Views

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, (2)
"Wonderful "
United States
Nolufefe Z.
The price is AU$602
includes taxes & fees
6 Jan - 7 Jan 2026
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is AU$1,993
includes taxes & fees
12 Dec - 13 Dec
Beechmont - Perfect for Family Retreat!

Peaceful apartment on 3.5 acres w/ artist studio.

Peaceful apartment on 3.5 acres w/ artist studio.
Brookfield
9.6 out of 10, Exceptional, (20)
"This was a nice get away for us that was not too far away from home."
United States
Isabella M.
The price is AU$293
includes taxes & fees
14 Dec - 15 Dec
Peaceful apartment on 3.5 acres w/ artist studio.
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 Westport Hotel Reviews

Find out more about Westport

Everything you need to know about Westport holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Westport holiday rental for you. At Expedia, you can take your pick from private holiday 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 Westport holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Westport holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westport. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Westport holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westport holiday rentals we have selected for you start as low as AU$206 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Westport rentals

At Expedia, we put the best Westport holiday 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 Westport 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 Westport holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Westport. 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 holiday rentals in Westport?

Yes, there are holiday rentals in Westport close to Earthplace Museum, or you can select a more secluded option if you're looking for a relaxing stay. Westport is known for its football games and waterfront. Make sure you have time to check out the entertainment choices and theatres during your trip.

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

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.: This holiday home rental outside of Westport 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 holiday rentals will I find in Westport?

Expedia has 58 holiday rentals for your stay in Westport.

What’s there to see and do in Westport?

Family-friendly attractions include Earthplace Museum and Rolnick Observatory, whereas Compo Beach and Old Mill Beach are a couple of great spots to enjoy the outdoors. Levitt Pavilion and Westport Country Playhouse are other places to visit while you're in town.

What’s a holiday rental in Westport like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Westport. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for small groups.