Westport Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Westport vacation rentals

1 bedroom, desk, WiFi, bed sheets

Apartment in Westport

Spacious Studio with Pool Table
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
$271 nightly
The price is $295
Apr 1 - Apr 2
Total with taxes and fees
Spacious Studio with Pool Table
Property grounds

Vacation Home in Greenwich

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
$239 nightly
The price is $271
Mar 10 - Mar 11
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Smart TV

Vacation Home in Brooklawn - St. Vincent

Centric property close to all the great things in the city
7.0 out of 10, Good, (14 reviews)
"This rental was great accommodation"
United States
Alma B.
$265 nightly
The price is $299
Mar 12 - Mar 13
Total with taxes and fees
Centric property close to all the great things in the city
Interior

Vacation Home in Milford

42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!
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
$371 nightly
The price is $371
Mar 12 - Mar 13
Total with taxes and fees
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!
1 bedroom, iron/ironing board, free WiFi, bed sheets

Vacation Home in Shelton

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
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.
$173 nightly
The price is $196
Mar 10 - Mar 11
Total with taxes and fees
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Property grounds

Vacation Home in Waterside

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
$288 nightly
The price is $326
Mar 11 - Mar 12
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Marina

Vacation Home in Cold Spring Harbor

Captain's Cottage - Cold Spring Harbor Water Views
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.
$424 nightly
The price is $484
Mar 17 - Mar 18
Total with taxes and fees
Captain's Cottage - Cold Spring Harbor Water Views
Fridge, microwave, stovetop, cookware/dishes/utensils

Apartment in Brooklawn - St. Vincent

Zen, Spacious & Comfy 2 bed, Lux beds
$288 nightly
The price is $326
Mar 11 - Mar 12
Total with taxes and fees
Zen, Spacious & Comfy 2 bed, Lux beds
Interior

Apartment in Downtown Bridgeport

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
10.0 out of 10, Exceptional, (4 reviews)
"Nice little spot with a great host."
United States
J M.
$181 nightly
The price is $205
Mar 10 - Mar 11
Total with taxes and fees
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Property grounds

Apartment in Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck 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.
$137 nightly
The price is $154
Mar 10 - Mar 11
Total with taxes and fees
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Exterior

Apartment in Kings Park

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
10.0 out of 10, Exceptional, (18 reviews)
"Perfect spot for a quick trip"
United States
James P.
$157 nightly
The price is $179
Apr 9 - Apr 10
Total with taxes and fees
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
TV, offices

Apartment in Milford

Beach Apartment in Woodmont Milford 102
$241 nightly
The price is $273
Mar 10 - Mar 11
Total with taxes and fees
Beach Apartment in Woodmont Milford 102
Pool

Vacation Home in Stratford

Business or Weekend escape
9.2 out of 10, Wonderful, (53 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
$130 nightly
The price is $147
Mar 26 - Mar 27
Total with taxes and fees
Business or Weekend escape
Property grounds

Apartment in Cove - East Side - Shippan

Seabreeze at the beach west beach Stamford ct.
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
$351 nightly
The price is $398
Mar 12 - Mar 13
Total with taxes and fees
Seabreeze at the beach west beach Stamford ct.
1 bedroom, WiFi

Apartment in Huntington Station

Luxe Provincial Style Studio w/ Patio & Parking
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
$334 nightly
The price is $382
Mar 10 - Mar 11
Total with taxes and fees
Luxe Provincial Style Studio w/ Patio & Parking
5 bedrooms, desk, iron/ironing board, travel crib

Vacation Home in Brooklawn - St. Vincent

The B&W Haven 5BR Home with yard theater + Office
9.4 out of 10, Exceptional, (8 reviews)
"Lovely home with plenty of room! "
United States
David S.
$593 nightly
The price is $672
Mar 15 - Mar 16
Total with taxes and fees
The B&W Haven 5BR Home with yard theater + Office
Classic Suite | Iron/ironing board, free WiFi, bed sheets

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (80 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
$225 nightly
The price is $258
Mar 15 - Mar 16
Total with taxes and fees
DUNE Fairfield Beach
TV

Apartment in Port Chester

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
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
$325 nightly
The price is $372
Mar 11 - Mar 12
Total with taxes and fees
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
TV, fireplace, books, offices

Vacation Home in Cove - East Side - Shippan

New Beach Home near Stamford Downtown/Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Great stay!"
United States
Kyra S.
$818 nightly
The price is $869
Mar 11 - Mar 12
Total with taxes and fees
New Beach Home near Stamford Downtown/Shippan
Fridge, microwave, oven, stovetop

Vacation Home in Fairfield

Renovated Cape Near beach, with Fire Pit and BBQ
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.
$429 nightly
The price is $486
Mar 10 - Mar 11
Total with taxes and fees
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

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

10/10 Excellent
"The King size bed was fine, We requested the mattress on the convertible couch to be changed, and they accommodated us. Staff was very service oriented. Included breakfast was very good. The room was clean, quite spacious, and comfortable. As in most places, noise can be an issue with paper thin walls. Overall experience was excellent!!! "
Esther 3-night trip
Posted 1 hour ago
Hyatt Place Milford / New Haven

Find out more about Westport

Everything you need to know about Westport 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 Westport vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Westport vacation 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 low season months. For more hustle and bustle, you may prefer to visit Westport in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $147 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Westport rentals

At Expedia, we put the best Westport 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 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 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 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 vacation rentals in Westport?

Yes, there are vacation rentals in Westport near Westport Arts Center, or you can choose a more secluded option if you want a relaxing stay. Westport is known for its football games and waterfront. Make sure you have time to check out the entertainment choices and theaters during your trip.

What are some of the best vacation rentals in Westport?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation home rental near 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 vacation rentals will I find in Westport?

Expedia has 58 vacation 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 vacation rental in Westport like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Westport. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.