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Westport Vacation Rentals

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Vacation Rentals in Westport

Outdoor pool, a heated pool
Westport Paradise With Every Amenity!
10.0 out of 10, Exceptional, (12)
"Super clean, comfortable, and great for overnight stay. Will definitely be back!"
The price is $559
$807 total
includes taxes & fees
May 20 - May 21
Westport Paradise With Every Amenity!
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach
3.0 star property
10.0 out of 10, Exceptional, (10)
"Modern cottage near the beach. Clean and comfortable. Very responsive."
The price is $181
$310 total
includes taxes & fees
May 28 - May 29
DUNE Fairfield Beach
Property grounds
Lake Luxury
10.0 out of 10, Exceptional, (8)
"We loved our stay at this home. Plenty of space so we didn’t feel like we were on top of each other, gorgeous kitchen (plus a separate butler’s kitchen!), and lux bathrooms made this rental exactly what we needed. Thanks Gianna!"
Lake Luxury
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Terrace/patio
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (103)
"Pleasant stay"
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Beach nearby, beach towels
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (14)
"We loved our stay at the bungalow last weekend. Donna equipped the home with everything needed for a comfortable stay, and more. It is located in a quiet area steps from the Milford Point Audubon center, Wheeler Marsh and Cedar beach. We walked to the Walnut Beach area where there are a few shops and restaurants, most notably a delicious Mexican restaurant and coffee shop. A perfect get away, despite the questionable weather."
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Beach nearby
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
10.0 out of 10, Exceptional, (1)
"The location within walking distance church"
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (15)
"We so enjoyed our stay! The house was perfect for our family, conveniently located close to extended family and with the most beautiful view. The house had everything we needed and provided the perfect home base for spring break in our hometown. We even got to experience an earth quake ;) thank you!!"
Serenity Awaits at this Cozy Lakeside Bungalow
Fridge, microwave, oven, stovetop
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
10.0 out of 10, Exceptional, (12)
"Stayed at Coastal Retreat for a weekend visit with son who attends Fairfield University, brought both sets of parents and teen daughter (ages ranging 73-16), plenty of room and able to enjoy a wonderful family dinner with son even in attendance. Wonderful area, close walk to beach and easy to get to downtown Fairfield and university. Very clean and welcoming! Greg was wonderful to work with and answered any question we had that came up both prior and upon arrival. The only thing we would mention...
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
3 bedrooms, desk, WiFi, bed sheets
Direct Beachfront Property On Long Island Sound
10.0 out of 10, Exceptional, (26)
"We had a wonderful time on the beach, in the ocean and just relaxing in the house. There were nice restaurants in the area to try and some fun day trips to take with the kids. We'd go back!"
Direct Beachfront Property On Long Island Sound
Beach nearby, sun loungers, beach towels
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
10.0 out of 10, Exceptional, (11)
"Enjoyed the house and the location! Would stay again!"
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
Fridge, microwave, stovetop, coffee/tea maker
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
10.0 out of 10, Exceptional, (3)
"We went to a show at the Capital Theater and this place was very convenient. Had a nice dinner in walking distance as well. The building is old and kind of gross, but the apartment itself was very nice, modern, and clean."
The price is $150
$272 total
includes taxes & fees
May 31 - Jun 1
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Beach
The Safe House - High Tech Apt #2 - 3 Beds
10.0 out of 10, Exceptional, (29)
"Since it was first time with VRBO, I was a little nervous about the whole process going into it. Rob was great to answer questions and deal with both myself and my granddaughter.It was an ideal location for visiting the Hudson River Valley and along the coast to Newport. We flew into White Plains and it is just a 20 minute ride away. The apartment was clean and convenient. We only ate 3 meals in 5 days away from there. The beds were comfortable and the shower was very nice. I liked the shower...
The price is $106
$213 total
includes taxes & fees
May 27 - May 28
The Safe House - High Tech Apt #2 - 3 Beds
Beach
The Safe House - High Tech Apt #3 - 4 beds
10.0 out of 10, Exceptional, (32)
"Exactly like pictures, clean, good location for visiting friends in southern CT and spending day in the city."
The price is $130
$239 total
includes taxes & fees
May 23 - May 24
The Safe House - High Tech Apt #3 - 4 beds
Fridge, microwave, oven, stovetop
Adorable 1-Bedroom Cottage in Weston, CT
10.0 out of 10, Exceptional, (24)
"Clean, Safe, and Comfortable! Thank you Jacques for the convenience of staying near Westport !"
The price is $195
$302 total
includes taxes & fees
May 19 - May 20
Adorable 1-Bedroom Cottage in Weston, CT
Beach nearby, sun loungers
Life is Better at the Beach!
10.0 out of 10, Exceptional, (23)
"Nice weekend with friends and young kids. The place is family friendly, clean and has a great atmosphere. Audrey and her husband were very communicative and welcoming! We loved our stay"
Life is Better at the Beach!
Aerial view
Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (37)
"Came into town for Passover in Syosset, this was a great home to stay in for the long weekend. Beautiful location with lots in walking distance so we could enjoy the area. Kitchen amazingly well stocked to be able to help with cooking. As others have mentioned, the stairs to one of the King bedrooms are very steep so at least 2 guests need to be able to essentially go up and down a ladder- our guest mix made this fine. Backyard seating area was beautiful with direct access to Cold Spring Harbor...
The price is $281
$541 total
includes taxes & fees
May 28 - May 29
Captain's Cottage - Cold Spring Harbor Water Views
Interior
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
10.0 out of 10, Exceptional, (40)
"We were in town to celebrate my son's college graduation, and stayed at this beautiful home about 30 minutes from Quinnipiac University. The house was very clean and the check in process was smooth. Stacie was extremely responsive to our inquiries, despite being on vacation in a different time zone. The sitting room area overlooked the Long Island sound, and the master bedroom and kitchen also had beautiful views. The house was stocked with some board games, and also outdoor games (Spikeball,...
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
3 bedrooms, desk, iron/ironing board, free WiFi
Private Waterfront Home on Long Island’s North Shore Northport Village NY
10.0 out of 10, Exceptional, (1)
"You cannot beat the beautiful views that this lovely home has to offer . The owner Richard could not be more attentive and accomidating. Northport is a fabulous town with so much to do . We would return in the future❤️❤️❤️"
Private Waterfront Home on Long Island’s North Shore Northport Village NY
Property grounds
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, (15)
"From the moment we came we felt right at home! Such a comfortable place to stay! Every morning we were greeted by a beautiful bald eagle on the lake as well as the chitter chatter of birds. For those who have a hard time climbing stairs, this is NOT the place for you. Bedrooms as well as bathrooms are not on the main level. No matter we would definitely want to stay again!"
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Fridge, microwave, oven, stovetop
Sunny Studio APT above historic Westport Mill
9.8 out of 10, Exceptional, (57)
"Had a wonderful stay!!"
Sunny Studio APT above historic Westport Mill
Don't see what you're looking for?
See all available properties in Westport
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.

Westport Vacation Rental Travel Info

Number of vacation rentals
7
Popular accommodation
Westport private vacation homes
Known landmarks
Norwalk Maritime Aquarium, Jennings Beach and Compo Beach
International airports
New York, NY (JFK-John F. Kennedy Intl.), Islip, NY (ISP-MacArthur) and White Plains, NY (HPN-Westchester County)

Other types of properties in Westport you may be interested in

Outdoor wedding area
Inn at Longshore
2.5 star property
9.2 out of 10, Wonderful, (106)
"Lovely "
The price is $169
$194 total
includes taxes & fees
May 17 - May 18
Inn at Longshore
Front of property
Amsterdam Hotel
2.0 star property
8.4 out of 10, Very Good, (1501)
"Pretty decent although an older property. Help very friendly. Breakfast included but they need better bagels."
The price is $90
$105 total
includes taxes & fees
May 20 - May 21
Amsterdam Hotel
Bicycling
EVEN Hotel Norwalk, an IHG Hotel
3.5 star property
8.4 out of 10, Very Good, (1004)
"Excellent customer service "
The price is $125
$144 total
includes taxes & fees
Jun 10 - Jun 11
EVEN Hotel Norwalk, an IHG Hotel
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.

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 $80 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.

Frequently asked questions

Can I find vacation rentals in Westport?

Yes, there are vacation rentals in Westport near Earthplace Museum, 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?

Business or Weekend escape: This vacation home rental near Westport has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals will I find in Westport?

Expedia has 54 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 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 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.

Recent reviews of Westport properties
Expedia verified reviews

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

5/5 Excellent
"Older property. The suites look impressive but regular rooms are just okay. Small bathrooms and squeaky beds"
A verified traveler stayed at Norwalk Inn & Conference Center
Posted 3 days ago
Norwalk Inn & Conference Center