A calm river reflecting buildings and trees, with a clear sky above.

Westport Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Westport vacation rentals

1 bedroom, desk, WiFi, bed sheets

1. 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
$237 nightly
The price is $257
Aug 28 - Aug 29
Total with taxes and fees
Spacious Studio with Pool Table
Interior

2. Nama-stay, sweet pink Saugatuck Shores beach cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.2 out of 10, Wonderful, (17 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
$617 nightly
The price is $698
Sep 24 - Sep 25
Total with taxes and fees
Nama-stay, sweet pink Saugatuck Shores beach cottage
Standard Room, 1 King Bed, Main Building | Property entrance

3. 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
$344 nightly
The price is $396
Sep 1 - Sep 2
Total with taxes and fees
Guesthouse at Norwalk Inn
Classic Suite | Iron/ironing board, WiFi (free), bed sheets

4. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (111 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
$233 nightly
The price is $268
Sep 13 - Sep 14
Total with taxes and fees
DUNE Fairfield Beach
Smart TV, fireplace, books, stereo

5. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (15 reviews)
"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."
United States
Melissa H.
$630 nightly
The price is $713
Aug 30 - Aug 31
Total with taxes and fees
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Dining

6. King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great "
United States
Ricky W.
$319 nightly
The price is $361
Aug 30 - Aug 31
Total with taxes and fees
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Interior

7. Modern Apartment with Private Entrance

Modern Apartment with Private Entrance
Historic District
$240 nightly
The price is $272
Aug 30 - Aug 31
Total with taxes and fees
Modern Apartment with Private Entrance
Living area

8. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
$382 nightly
The price is $432
Aug 30 - Aug 31
Total with taxes and fees
Gilded Age Luxury Surrounded by Nature
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

9. 2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
$309 nightly
The price is $350
Sep 7 - Sep 8
Total with taxes and fees
2-bedroom apartmet No cleaning Fee
House (4 Bedrooms) | Interior

10. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
$652 nightly
The price is $749
Aug 30 - Aug 31
Total with taxes and fees
4 Mi to Beach & Dtwn! Charming Fairfield Home
4 bedrooms, iron/ironing board, WiFi, bed sheets

11. 4 BR VILLA, celebration welcome, No Cleaning fee

4 BR VILLA, celebration welcome, No Cleaning fee
West Norwalk
$633 nightly
The price is $717
Aug 29 - Aug 30
Total with taxes and fees
4 BR VILLA, celebration welcome, No Cleaning fee
1 bedroom, desk, iron/ironing board, WiFi (free)

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

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (17 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
$205 nightly
The price is $232
Aug 28 - Aug 29
Total with taxes and fees
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Smart TV

13. Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
$856 nightly
The price is $968
Sep 21 - Sep 22
Total with taxes and fees
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
Beach nearby, sun loungers, beach towels

14. 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, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
$569 nightly
The price is $644
Sep 21 - Sep 22
Total with taxes and fees
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Front of property

15. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
$1,325 nightly
The price is $1,524
Aug 28 - Aug 29
Total with taxes and fees
Beechmont - Perfect for Family Retreat!
A heated pool

16. Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability

Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability
New Canaan
10.0 out of 10, Exceptional, (42 reviews)
"Unique home with beautiful grounds and classically designed interior. Perfect for relaxing and enjoying with family/friends."
United States
David
$2,086 nightly
The price is $2,364
Sep 7 - Sep 8
Total with taxes and fees
Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability
Interior

17. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
10.0 out of 10, Exceptional, (1 review)
"Beautiful home! Host was super responsive to questions. The entire house was super clean and welcoming. The bed was comfortable and smelled fresh. There was a personalized welcome sign that was a nice touch and some (much needed) snacks after our almost 3 hour drive. Expectations were well within reason and easily manageable. I would 100% rent again."
United States
Raelyn O.
$667 nightly
The price is $755
Aug 30 - Aug 31
Total with taxes and fees
4 Mi to Beach & Dtwn! Charming Fairfield Home
Exterior

18. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (168 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$151 nightly
The price is $174
Aug 30 - Aug 31
Total with taxes and fees
Stamford Suites
Interior

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

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.6 out of 10, Exceptional, (26 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveler
$364 nightly
The price is $412
Sep 14 - Sep 15
Total with taxes and fees
Luxury Designer 2 bedroom+office/3bed vacation home.
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

Hilton Garden Inn Milford

Hilton Garden Inn Milford

8/10 Good
"We stayed here for two nights when we were getting our house renovated. It was on our short list of hotels that accepted dogs that were 75 or more pounds. We have two German shepherds. The hotel had a lot of outdoor space to walk the dogs and had poopy bags and garbage outside. The staff was very friendly. We were on the first floor and had easy access to an exit door a few hundred feet from my room to easily walk the dogs. There is a small gym that was nice that I used the treadmill at. There’s a pool right next to the gym that we did not use, but it looked nice and clean. The room was nice. For a standard room it was on the bigger side. It had a small refrigerator, Keurig, coffee machine, and microwave. The bed was comfortable, but not the most comfortable I’ve slept on. The pillows were not very comfortable. There was a nice desk and the air conditioning worked well. There were electrical outlets and USB chargers to charge your devices on one of the nightstands. The shower and bathroom were clean. The water pressure in the shower was OK. There was a lot of counter space on the vanity to put toiletries. The main thing I did not like was that when you turned the bathroom light on it had a really loud fan. It would’ve been nice if there were separate switches for the fan and light. The Room was clean. There is a restaurant that we had grilled chicken sandwiches at one night that were really good. Overall, a nice three star property."
allison 2-night trip
Posted 9 hours ago
Hilton Garden Inn Milford

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 $156 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?

Charming Home in Seaside: This vacation home rental near Westport is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Westport?

Expedia has 55 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.