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Westport Vacation Rentals

Vacation Rentals in Westport

Westport Paradise With Every Amenity!
Outdoor pool, a heated pool
Westport Paradise With Every Amenity!
10.0 out of 10, Exceptional, (14)
"The guest house was spacious and well appointed. The furnishings were very comfortable. The grounds at the house are beautiful. We thoroughly enjoyed our stay."
The price is $585
$841 total
includes taxes & fees
Jun 12 - Jun 13
Westport Paradise With Every Amenity!
Sunny Studio APT above historic Westport Mill
Fridge, microwave, oven, stovetop
Sunny Studio APT above historic Westport Mill
9.8 out of 10, Exceptional, (59)
"Gerard prioritizes guest comfort and is an excellent communicator. The Westport Studio is our second stay at one of his quality properties, the other was in Mystic Connecticut. We look forward to exploring more of his Great Gull, New England properties during our next trip along the East Coast. The Westport Studio, Old Mill and the Mystic School House, are well-equipped for eating in, the beds comfortable and the linens are high-quality. It is such a pleasure when a host takes care to provide...
Sunny Studio APT above historic Westport Mill
Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants
Microwave, stovetop, dishwasher, coffee/tea maker
Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants
Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants
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Stamford Suites
Exterior
Stamford Suites
2.5 star property
6.8 out of 10, (719)
"Inside the room in the hotel was very good and clean , We like to live here ."
The price is $169
$195 total
includes taxes & fees
Jun 18 - Jun 19
Stamford Suites
Business or Weekend escape
Pool
Business or Weekend escape
9.6 out of 10, Exceptional, (12)
"The place was clean. Very comfortable. He had refreshments in the fridge. 2nd time here. The host is very easy to get to answer from. We are coming back again soon."
The price is $75
$135 total
includes taxes & fees
Jun 12 - Jun 13
Business or Weekend escape
DUNE Fairfield Beach
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach
3.0 star property
10.0 out of 10, Exceptional, (11)
"Modern cottage near the beach. Clean and comfortable. Very responsive."
The price is $209
$296 total
includes taxes & fees
Jun 10 - Jun 11
DUNE Fairfield Beach
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Terrace/patio
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (104)
"Neighborhood great for walking dogs. Would have loved a sink besides bathroom. Overall great value."
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Luxury Designer 2 bedroom+office/3bed vacation home.
Terrace/patio
Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (10)
"Had a great stay!"
The price is $128
$397 total
includes taxes & fees
Jun 24 - Jun 25
Luxury Designer 2 bedroom+office/3bed vacation home.
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Beach nearby, beach towels
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (15)
"Donna, the host, was absolutely wonderful. Very responsive. Cute beach bungalow. Very comfortable. Perfect for the three of us, 2 adults and 19 year old daughter. Would absolutely recommend."
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Serenity Awaits at this Cozy Lakeside Bungalow
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (18)
"Stayed while attending a local wedding and wished we had had more time to hang out at the house! The lake is beautiful and the house had everything we needed! Hope to come back some day!"
Serenity Awaits at this Cozy Lakeside Bungalow
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
Beach nearby
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
10.0 out of 10, Exceptional, (2)
"Amazing place to stay people are great"
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
The Safe House - High Tech Apt #2 - 3 Beds
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 Safe House - High Tech Apt #2 - 3 Beds
Guesthouse at Norwalk Inn
Studio Suite, Kitchen | Private kitchen | Mini-fridge, coffee/tea maker
Guesthouse at Norwalk Inn
3.5 star property
8.4 out of 10, Very Good, (37)
"The pictures are very deceiving - as they are of the Guesthouses not the main hotel. I thought I was booking at an Inn, but I was really booked at a regular ole chain hotel. One that charges $8 per person per day for their pool! (you should really change this policy for paying overnight guests - why should we pay additional for facilities like this?) There's also nowhere to walk to from here, so if you're without a car expect to be paying for Ubers everywhere (which is fine as they're readily...
The price is $226
$260 total
includes taxes & fees
Jun 23 - Jun 24
Guesthouse at Norwalk Inn
Direct Beachfront Property On Long Island Sound
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
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
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
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
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
Cheerful 4 bedrooms residential house.
Fridge, microwave, dishwasher, coffee/tea maker
Cheerful 4 bedrooms residential house.
9.8 out of 10, Exceptional, (13)
"This was walking distance to the Total Mortgage Arena for our robotics competition. Having the full kitchen to cook meals was awesome. Nice comfy beds, plenty of space, I claimed the nook off the kitchen/dining area for myself. Boys had front room to work on their robot."
Cheerful 4 bedrooms residential house.
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient 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
$268 total
includes taxes & fees
Jun 30 - Jul 1
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
Property grounds
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
The price is $221
$307 total
includes taxes & fees
Jun 11 - Jun 12
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
Captain's Cottage - Cold Spring Harbor Water Views
Aerial view
Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (39)
"I rented this home for a multi-family vacation. We all absolutely loved the house. The beautiful view of the habor was amazing to see out the windows, porches, and backyard. The next door neighbors are very friendly. The house is very beautiful inside and comfortable. Bed upstairs was soft, king bed on the main floor is medium firm. The single beds on main floor one is soft one really firm. The playhouse in the backyard was the highlight for my grandson and made his vacation so special. In...
The price is $391
$685 total
includes taxes & fees
Jun 13 - Jun 14
Captain's Cottage - Cold Spring Harbor Water Views
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

Inn at Longshore
Outdoor wedding area
Inn at Longshore
2.5 star property
9.2 out of 10, Wonderful, (109)
"Lovely "
The price is $219
$252 total
includes taxes & fees
Jun 13 - Jun 14
Inn at Longshore
Westport Paradise With Every Amenity!
Outdoor pool, a heated pool
Westport Paradise With Every Amenity!
10.0 out of 10, Exceptional, (14)
"The guest house was spacious and well appointed. The furnishings were very comfortable. The grounds at the house are beautiful. We thoroughly enjoyed our stay."
The price is $585
$841 total
includes taxes & fees
Jun 12 - Jun 13
Westport Paradise With Every Amenity!
Amsterdam Hotel
Front of property
Amsterdam Hotel
2.0 star property
8.4 out of 10, Very Good, (1522)
"The staff was really nice. Customer service is definitely their highest priority. "
The price is $100
$116 total
includes taxes & fees
Jun 9 - Jun 10
Amsterdam 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 $75 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

The Stamford Hotel

The Stamford Hotel

5/5 Excellent
"Parking and food expensive but cleanliness and kind staff made up for it. "
A verified traveler stayed at The Stamford Hotel
Posted 2 days ago
The Stamford Hotel