Photo by Marina Timo

Westport Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Rentals in Westport

Our top choices for Westport vacation rentals

Stamford Suites

4.0 star property
5.6 out of 10, (49)
"Excellent sleep"
The price is CA $183
CA $210 total
includes taxes & fees
Sep 1 - Sep 2
Stamford Suites

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (67)
"Incredible staff, friendly, helpful. "
The price is CA $230
CA $349 total
includes taxes & fees
Sep 3 - Sep 4
DUNE Fairfield Beach

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
The price is CA $214
CA $415 total
includes taxes & fees
Sep 3 - Sep 4
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Business or Weekend escape

9.2 out of 10, Wonderful, (45)
"We had stayed at Mansoor's a few weeks ago and returned this past weekend. Once again, we found the place spotless, comfortable and well-stocked. We really like this place and expect to return again in the future. "
The price is CA $118
CA $203 total
includes taxes & fees
Sep 14 - Sep 15
Business or Weekend escape

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
The price is CA $347
CA $400 total
includes taxes & fees
Sep 14 - Sep 15
Guesthouse at Norwalk Inn

Waterfront Breathtaking Cozy Beach Cottage Sunsets Inspiring Peaceful 1 hr NYC

9.0 out of 10, Wonderful, (7)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
The price is CA $454
CA $727 total
includes taxes & fees
Sep 3 - Sep 4
Waterfront Breathtaking Cozy Beach Cottage Sunsets Inspiring Peaceful 1 hr NYC

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (17)
"cleanliness. quiet. "
Luxury Apartments by Hyatus at The Asher

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (124)
"The house is beautiful, and one of the most unique and homey places we have everything stayed. Very spacious with lots of artwork, and arts and crafts style woodwork. The view of the sound is so serene. We enjoyed very much sitting out on the porch and gazing at the water and the passerbys, and taking walks along the sound. It has everything you need and then some. Thank you so much for sharing your gracious and beautiful home with us!"
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

10.0 out of 10, Exceptional, (2)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
The price is CA $996
CA $1,911 total
includes taxes & fees
Aug 28 - Aug 29
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

Luxury Designer 2 bedroom+office/3bed vacation home.

9.4 out of 10, Exceptional, (20)
"Had a great stay!"
The price is CA $205
CA $580 total
includes taxes & fees
Sep 1 - Sep 2
Luxury Designer 2 bedroom+office/3bed vacation home.

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very good, (12)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!

Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC

The price is CA $1,107
CA $1,478 total
includes taxes & fees
Sep 3 - Sep 4
Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC

Modern House in Black Rock

2.0 star property
9.0 out of 10, Wonderful, (6)
"Very easy stay and great location convenient to Fairfield University . Plenty of options to walk to for coffee or meals. Had everything we needed. Clean, well equipped. Great communication with owners. "
Modern House in Black Rock

Centric property close to all the great things in the city

7.6 out of 10, Good, (12)
"This rental was great accommodation"
The price is CA $218
CA $414 total
includes taxes & fees
Aug 28 - Aug 29
Centric property close to all the great things in the city

Adorable Beach Cottage

10.0 out of 10, Exceptional, (44)
"This property is perfect for two or 3 adults. Charming cottage, very clean, great beach community. "
Adorable Beach Cottage

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (5)
The price is CA $552
CA $1,000 total
includes taxes & fees
Aug 30 - Aug 31
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

10.0 out of 10, Exceptional, (2)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
The price is CA $194
CA $314 total
includes taxes & fees
Sep 2 - Sep 3
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (33)
"House was very clean and maintained. We needed to check in a day later and the host was very accommodating. Overall a great place to stay! "
Cheerful 4 bedrooms residential house.

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (63)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Charming 1-bedroom house in lovely Stony Brook with AC

Charming 1-bedroom house in lovely Stony Brook with AC
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

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, 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 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Westport vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westport vacation rentals we have selected for you start as low as CA $118 per night. Entering your travel dates in the search wizard 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 is equipped with a barbecue grill, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave, and a coffee maker.

How many vacation rentals will I find in Westport?

Expedia has 56 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.