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Westport Vacation Rentals

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In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Westport vacation rentals

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Stamford Suites

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (86)
"Everything was good other than the two options for breakfast and housekeeping entering the hotel room unannounced or no knocking"
United States
Laila
$130 nightly
The price is $150
Jan 5 - Jan 6
Total with taxes and fees
Stamford Suites
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
$252 nightly
The price is $290
Jan 19 - Jan 20
Total with taxes and fees
DUNE Fairfield Beach
2 bedrooms, iron/ironing board, travel crib, WiFi
Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
$254 nightly
The price is $288
Jan 5 - Jan 6
Total with taxes and fees
Renovated 2BR Retreat / Modern Comforts Included
Fridge, microwave, oven, stovetop
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (1)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
$276 nightly
The price is $313
Jan 27 - Jan 28
Total with taxes and fees
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Standard Room, 1 King Bed, Main Building | Property entrance
Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (41)
"it was amazing will stay again food was good comfort was great "
United States
anthony
$294 nightly
The price is $339
Jan 14 - Jan 15
Total with taxes and fees
Guesthouse at Norwalk Inn
Fridge, microwave, oven, stovetop
Beach Apartment in Woodmont Milford

Beach Apartment in Woodmont Milford

Beach Apartment in Woodmont Milford
2.0 star property
Milford
9.0 out of 10, Wonderful, (2)
"Had a great stay!"
United States
Garry G.
$336 nightly
The price is $381
Jan 7 - Jan 8
Total with taxes and fees
Beach Apartment in Woodmont Milford
Fridge, microwave, oven, stovetop
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Brooklawn - St. Vincent
8.0 out of 10, Very Good, (1)
"It was clean "
United States
Burton
$254 nightly
The price is $288
Jan 5 - Jan 6
Total with taxes and fees
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Fridge, microwave, oven, stovetop
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
10.0 out of 10, Exceptional, (2)
"Wonderful "
United States
Nolufefe Z.
$313 nightly
The price is $354
Jan 5 - Jan 6
Total with taxes and fees
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
Fridge, microwave, oven, stovetop
Bright Escape, Top-Rated Design, Fire pit, Near Beach

Bright Escape, Top-Rated Design, Fire pit, Near Beach

Bright Escape, Top-Rated Design, Fire pit, Near Beach
Fairfield
10.0 out of 10, Exceptional, (11)
"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.
$415 nightly
The price is $480
Jan 19 - Jan 20
Total with taxes and fees
Bright Escape, Top-Rated Design, Fire pit, Near Beach
1 bedroom, desk, iron/ironing board, free WiFi
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
10.0 out of 10, Exceptional, (4)
"Nice little spot with a great host."
United States
J M.
$186 nightly
The price is $211
Jan 7 - Jan 8
Total with taxes and fees
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Outdoor dining
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Fairfield
10.0 out of 10, Exceptional, (24)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
$436 nightly
The price is $494
Jan 11 - Jan 12
Total with taxes and fees
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
2.0 star property
Kings Park
10.0 out of 10, Exceptional, (17)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
$159 nightly
The price is $182
Jan 6 - Jan 7
Total with taxes and fees
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Beach
Spacious 4-bedroom house with WiFi and AC in awesome Milford

Spacious 4-bedroom house with WiFi and AC in awesome Milford

Spacious 4-bedroom house with WiFi and AC in awesome Milford
Milford
10.0 out of 10, Exceptional, (3)
"Wonderful beach house. We loved staying here! The house is a historic gem and the accommodations were perfect. We enjoyed fabulous fireworks on the deck and walking the beach each morning. We can’t wait to go back. "
United States
Jane S.
$625 nightly
The price is $708
Jan 5 - Jan 6
Total with taxes and fees
Spacious 4-bedroom house with WiFi and AC in awesome Milford
Fridge, microwave, oven, stovetop
Marine Theme - 4 BR - Backyard - Fire pit

Marine Theme - 4 BR - Backyard - Fire pit

Marine Theme - 4 BR - Backyard - Fire pit
North End
9.8 out of 10, Exceptional, (8)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
$346 nightly
The price is $393
Jan 5 - Jan 6
Total with taxes and fees
Marine Theme - 4 BR - Backyard - Fire pit
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.6 out of 10, Exceptional, (24)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
$227 nightly
The price is $257
Jan 7 - Jan 8
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Property grounds
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.4 out of 10, Exceptional, (20)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
$656 nightly
The price is $742
Jan 5 - Jan 6
Total with taxes and fees
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Property grounds
Luxury Designer 2 bedroom+office/3bed vacation home.

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

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (22)
"We stayed here for three nights, and it was very comfortable, clean and spacious. It's in a good location and the walk up to the second floor was not too bad. It was as advertised, and we would stay there again when in Bridgeport. "
United States
Robert C.
$380 nightly
The price is $431
Feb 2 - Feb 3
Total with taxes and fees
Luxury Designer 2 bedroom+office/3bed vacation home.
2 bedrooms, iron/ironing board, WiFi, bed sheets
Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.

Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.

Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.
Downtown Bridgeport
9.0 out of 10, Wonderful, (2)
"Very convenient location to everything in Bridgeport. Very easy and explicit check in directions! The unit was very clean!"
United States
Kelly
$337 nightly
The price is $382
Jan 5 - Jan 6
Total with taxes and fees
Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.
TV, offices
Beach Apartment in Woodmont Milford 102

Beach Apartment in Woodmont Milford 102

Beach Apartment in Woodmont Milford 102
2.0 star property
Milford
$311 nightly
The price is $353
Jan 5 - Jan 6
Total with taxes and fees
Beach Apartment in Woodmont Milford 102
Fridge, microwave, oven, stovetop
Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
$322 nightly
The price is $365
Jan 11 - Jan 12
Total with taxes and fees
Modern Luxe 1BR Apt in Downtown Stamford
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

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

10/10 Excellent
"Pet friendly with really nice staff"
Amy 2-night trip
Posted 2 days ago
EVEN Hotel Norwalk by IHG

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 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?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation home rental near Westport is equipped with a garden, air-conditioning, and a Smart TV 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 57 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 Old Mill 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.