Westport Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Westport vacation rentals

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
$245 nightly
The price is $266
May 11 - May 12
Total with taxes and fees
Spacious Studio with Pool Table

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
$1,197 nightly
The price is $1,376
May 11 - May 12
Total with taxes and fees
Beechmont - Perfect for Family Retreat!

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (86 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
$233 nightly
The price is $268
May 26 - May 27
Total with taxes and fees
DUNE Fairfield Beach

Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC
Northport
9.4 out of 10, Exceptional, (16 reviews)
"Our host, Richard, was exceptional. The home was charming, great location and perfect for us!"
United States
Laura H.
$1,019 nightly
The price is $1,165
May 12 - May 13
Total with taxes and fees
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Modern + Spacious 5BR/2BA Home, Renovated Backyard

Modern + Spacious 5BR/2BA Home, Renovated Backyard
West End - West Side
9.6 out of 10, Exceptional, (4 reviews)
"Used for family weekend at SHU. Convenient location and plenty of space for the whole family! "
United States
Laurene S.
$649 nightly
The price is $740
May 10 - May 11
Total with taxes and fees
Modern + Spacious 5BR/2BA Home, Renovated Backyard

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
9.6 out of 10, Exceptional, (9 reviews)
"Beautiful old home with tons of space!"
United States
Rebeccca H.
$1,526 nightly
The price is $1,726
May 10 - May 11
Total with taxes and fees
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

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, (76 reviews)
"Location was perfect!"
United States
Linda J P.
$465 nightly
The price is $531
May 11 - May 12
Total with taxes and fees
Captain's Cottage - Cold Spring Harbor Water Views

THE OASIS @ LONG ISLAND

THE OASIS @ LONG ISLAND
Huntington Station
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
$429 nightly
The price is $490
May 10 - May 11
Total with taxes and fees
THE OASIS @ LONG ISLAND

Beach Apartment in Woodmont Milford 102

Beach Apartment in Woodmont Milford 102
Milford
$305 nightly
The price is $344
May 11 - May 12
Total with taxes and fees
Beach Apartment in Woodmont Milford 102

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)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
$233 nightly
The price is $264
May 10 - May 11
Total with taxes and fees
Centric property close to all the great things in the city

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)
"Excellent home, met all expectations, and attentive staff"
United States
Steve G.
$740 nightly
The price is $786
May 12 - May 13
Total with taxes and fees
New Beach Home near Stamford Downtown/Shippan

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
$337 nightly
The price is $388
May 10 - May 11
Total with taxes and fees
Guesthouse at Norwalk Inn

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (32 reviews)
"Hosts were readily available to address any needs that arose. Home was comfortable for our weekend visit."
United States
Meg S.
$445 nightly
The price is $503
May 11 - May 12
Total with taxes and fees
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

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, (12 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
$308 nightly
The price is $349
May 10 - May 11
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.2 out of 10, Wonderful, (23 reviews)
"Great location for visiting Stamford, right on the water, a short walk from the beach, a short drive from the ShopRite. Liked the pool table. Excellent kitchen. Backyard seemed very nice but didn't use it due to weather. Easily parks 5 cars, and off-season (Oct-Apr) there is parking at the beach nearby."
United States
Eric K.
$843 nightly
The price is $896
May 18 - May 19
Total with taxes and fees
Waterview House Walking Distance from Cove Beach

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (54 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
$130 nightly
The price is $147
May 10 - May 11
Total with taxes and fees
Business or Weekend escape

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.
$199 nightly
The price is $226
May 8 - May 9
Total with taxes and fees
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Walkable Townhouse with Garage & Yard, 45 min to NYC!

Walkable Townhouse with Garage & Yard, 45 min to NYC!
West Side
9.4 out of 10, Exceptional, (6 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
$574 nightly
The price is $623
May 11 - May 12
Total with taxes and fees
Walkable Townhouse with Garage & Yard, 45 min to NYC!

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, (33 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
$283 nightly
The price is $321
May 20 - May 21
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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

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.

Frequently asked questions

Can I find vacation rentals in Westport?

Yes, there are vacation rentals in Westport near Rolnick Observatory, 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?

Spacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.: This Westport vacation home rental offers a fireplace, a hot tub, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

How many vacation rentals will I find in Westport?

Expedia has 59 vacation rentals for your stay in Westport.

What’s there to see and do in Westport?

Family-friendly attractions include Rolnick Observatory and Earthplace Museum, 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.