View across the Saugatuck River from Westport toward industrial buildings

Westport Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is AU$456
includes taxes & fees
5 July - 6 July
Spacious Studio with Pool Table

Spacious Family Home

Spacious Family Home
Westport
10.0 out of 10, Exceptional, (1 review)
"We had a getaway weekend for a close friend group from college. This location could not have been better! We had everything we needed. Four bedrooms and three full bathrooms and across the street, a bakery, pizza place, fantastically stocked market, and a nice restaurant! A short drive allowed us to enjoy shopping and more food choices, as well as giving our Manhattan friend easy access to the train. Really could not have been a better place for us. Communication with the host was timely,...
United States
Laura B.
The price is AU$1,750
includes taxes & fees
7 July - 8 July
Spacious Family Home

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, (11 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 AU$329
includes taxes & fees
16 June - 17 June
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
The price is AU$422
includes taxes & fees
24 June - 25 June
Zen, Spacious & Comfy 2 bed, Lux beds

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, (26 reviews)
"First of all the pictures didn't do this place any justice. I love the layout and size of this place, the rooms are spacious, the living room and dining areas are perfectly organized, and the kitchen and bathroom are huge, and everything we're cleaned and nothing out of place. Excellent job by host, nothing I can think of improving. I will definitely try booking this place again when I get the dates of our next event next year."
United States
Shamel
The price is AU$533
includes taxes & fees
11 June - 12 June
Luxury Designer 2 bedroom+office/3bed vacation home.

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
7.0 out of 10, Good, (14 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
The price is AU$384
includes taxes & fees
14 June - 15 June
Centric property close to all the great things in the city

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (91 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is AU$381
includes taxes & fees
29 June - 30 June
DUNE Fairfield Beach

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, (37 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AU$456
includes taxes & fees
11 June - 12 June
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (55 reviews)
"I love the layout of this apt. Perfect for 2 to 3 people, it was clean and nothing out of place. The host was great and communicated well. I will be looking for this place again next year."
United States
Shamel
The price is AU$212
includes taxes & fees
11 June - 12 June
Business or Weekend escape

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"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$487
includes taxes & fees
21 June - 22 June
Renovated 2BR Retreat / Modern Comforts Included

Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (4 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 AU$517
includes taxes & fees
11 June - 12 June
Modern 2 Bed in BlackRock

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (32 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is AU$589
includes taxes & fees
11 June - 12 June
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

beautiful Cozy 1BR Apt near New Haven

beautiful Cozy 1BR Apt near New Haven
Seymour
beautiful Cozy 1BR Apt near New Haven

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
9.2 out of 10, Wonderful, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is AU$551
includes taxes & fees
18 June - 19 June
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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 AU$698
includes taxes & fees
11 June - 12 June
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

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

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (21 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is AU$249
includes taxes & fees
17 June - 18 June
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Spacious Easton 2BR Townhouse with Big Yard

Spacious Easton 2BR Townhouse with Big Yard
Easton
Spacious Easton 2BR Townhouse with Big Yard

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 AU$590
includes taxes & fees
11 June - 12 June
Modern Luxe 1BR Apt in Downtown Stamford

Wonderful 3-bedroom apartment with AC in welcoming Bridgeport

Wonderful 3-bedroom apartment with AC in welcoming Bridgeport
Downtown Bridgeport
The price is AU$384
includes taxes & fees
24 June - 25 June
Wonderful 3-bedroom apartment with AC in welcoming Bridgeport

Solara – Luxury 1BR Downtown

Solara – Luxury 1BR Downtown
Downtown Stamford
The price is AU$577
includes taxes & fees
18 June - 19 June
Solara – Luxury 1BR Downtown
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.
Save an average of 15% on thousands of hotels when you're signed in

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$212 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. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Westport?

Yes, there are holiday rentals in Westport close to Westport Arts Center, 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?

Spacious Family Home: This highly rated holiday home rental in Westport has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in Westport?

Expedia has 55 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 Burying Hill 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.