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 reviews)
"There isn’t a “kitchen” but a minimum amenity was there and that was enough for me. Lots of dining options nearby. A quiet neighborhood and separate entry. Host was very responsive and accommodating. "
United States
Chihiro
The price is AU$412
includes taxes & fees
5 Apr - 6 Apr
Spacious Studio with Pool Table

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, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AU$388
includes taxes & fees
12 Mar - 13 Mar
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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)
"This rental was great accommodation"
United States
Alma B.
The price is AU$419
includes taxes & fees
12 Mar - 13 Mar
Centric property close to all the great things in the city

42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!
Milford
8.8 out of 10, Excellent, (9 reviews)
"Overall was a good stay, we stayed here for a work training. I would recommend this property for any type of occasion. The host was very attentive and hopeful as well."
United States
Rosseline
The price is AU$513
includes taxes & fees
12 Mar - 13 Mar
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

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 reviews)
"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$277
includes taxes & fees
12 Mar - 13 Mar
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

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
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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, (75 reviews)
"Perfect space for family. Enjoyed ping pong, walk to the village, hike in the park and view oh the harbor. "
United States
Randall S.
The price is AU$660
includes taxes & fees
18 Mar - 19 Mar
Captain's Cottage - Cold Spring Harbor Water Views

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
The price is AU$458
includes taxes & fees
13 Mar - 14 Mar
Zen, Spacious & Comfy 2 bed, Lux beds

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, (4 reviews)
"Nice little spot with a great host."
United States
J M.
The price is AU$259
includes taxes & fees
17 Mar - 18 Mar
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
7.6 out of 10, Good, (4 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is AU$220
includes taxes & fees
17 Mar - 18 Mar
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

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, (18 reviews)
"Perfect spot for a quick trip"
United States
James P.
The price is AU$258
includes taxes & fees
14 Mar - 15 Mar
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Beach Apartment in Woodmont Milford 102

Beach Apartment in Woodmont Milford 102
Milford
The price is AU$432
includes taxes & fees
12 Mar - 13 Mar
Beach Apartment in Woodmont Milford 102

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (53 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is AU$209
includes taxes & fees
26 Mar - 27 Mar
Business or Weekend escape

Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is AU$557
includes taxes & fees
12 Mar - 13 Mar
Seabreeze at the beach west beach Stamford ct.

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is AU$538
includes taxes & fees
13 Mar - 14 Mar
Luxe Provincial Style Studio w/ Patio & Parking

The B&W Haven 5BR Home with yard theater + Office

The B&W Haven 5BR Home with yard theater + Office
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (8 reviews)
"Lovely home with plenty of room! "
United States
David S.
The price is AU$946
includes taxes & fees
15 Mar - 16 Mar
The B&W Haven 5BR Home with yard theater + Office

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (80 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (30 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$536
includes taxes & fees
17 Mar - 18 Mar
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

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)
"Great stay!"
United States
Kyra S.
The price is AU$1,201
includes taxes & fees
12 Mar - 13 Mar
New Beach Home near Stamford Downtown/Shippan

Renovated Cape Near beach, with Fire Pit and BBQ

Renovated Cape Near beach, with Fire Pit and BBQ
Fairfield
10.0 out of 10, Exceptional, (11 reviews)
"Great clean, kid-friendly house in just the location we wanted. Lots of thoughtful touches throughout the house that made our stay very comfortable. Would stay again!"
United States
Mary G.
The price is AU$679
includes taxes & fees
12 Mar - 13 Mar
Renovated Cape Near beach, with Fire Pit and BBQ
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$209 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 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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of Westport is equipped with a garden, air conditioning and WiFi 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 Old Mill Beach and Compo 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.