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Westport Vacation Rentals

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Oct 25 - Oct 26
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Oct 26 - Oct 27
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Oct 31 - Nov 2
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Nov 7 - Nov 9

Vacation Rentals in Westport

Interior
Sweet Studio w/ Lounge & Pool Table
Sweet Studio w/ Lounge & Pool Table
8.8 out of 10, Excellent, (6)
"So cute and comfortable "
United States
Maria
The price is ￥18,769
￥38,560 total
includes taxes & fees
Oct 26 - Oct 27
Sweet Studio w/ Lounge & Pool Table
Lobby
Stamford Suites
Stamford Suites
4.0 star property
5.8 out of 10, (65)
"Location very good."
United States
Sheila
The price is ￥20,146
￥23,168 total
includes taxes & fees
Oct 26 - Oct 27
Stamford Suites
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach
DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (74)
"Loved this venue! "
United States
adriano
DUNE Fairfield Beach
Lounge
Luxury Apartments by Hyatus at The Asher
Luxury Apartments by Hyatus at The Asher
4.5 star property
10.0 out of 10, Exceptional, (18)
"This place truly felt like a home away from home. Everything was spotless, comfortable, and well cared for. The location made it easy to access everything we needed, whether dining, shopping, or exploring the area. I would definitely return!"
United States
Tasha
Luxury Apartments by Hyatus at The Asher
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
9.6 out of 10, Exceptional, (18)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is ￥9,888
￥28,461 total
includes taxes & fees
Oct 26 - Oct 27
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Standard Room, 1 King Bed, Main Building | Property entrance
Guesthouse at Norwalk Inn
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 "
United States
anthony
The price is ￥35,824
￥41,198 total
includes taxes & fees
Nov 3 - Nov 4
Guesthouse at Norwalk Inn
Pool
Business or Weekend escape
Business or Weekend escape
9.2 out of 10, Wonderful, (50)
"Great value!"
United States
Bruce H.
The price is ￥12,207
￥21,477 total
includes taxes & fees
Oct 26 - Oct 27
Business or Weekend escape
Outdoor dining
Beechmont - Perfect for Family Retreat!
Beechmont - Perfect for Family Retreat!
5.0 star property
The price is ￥103,178
￥172,062 total
includes taxes & fees
Oct 28 - Oct 29
Beechmont - Perfect for Family Retreat!
Smart TV, stereo
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!
10.0 out of 10, Exceptional, (3)
"Very clean house. set up very nicely, landlord was very responsive and helpful. perfect for what we needed "
United States
Nancy H.
The price is ￥109,865
￥210,956 total
includes taxes & fees
Oct 26 - Oct 27
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!
Property grounds
Luxury Designer 2 bedroom+office/3bed vacation home.
Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (22)
"Beautifully appointed luxury 2 nd floor accommodations in the city of Bridgeport. Guests could comfortably stay for multiple nights with the well equipped kitchen and dining room space. "
United States
Tessa P.
The price is ￥21,057
￥62,363 total
includes taxes & fees
Oct 27 - Oct 28
Luxury Designer 2 bedroom+office/3bed vacation home.
Property grounds
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
9.2 out of 10, Wonderful, (12)
"This is a quiet and beautiful spot on the water. The outside space is perfect to relax or get some sun. The inside space was relaxing and very comfortable. The host, Richard was wonderful and very responsive. "
United States
Lori G.
The price is ￥68,254
￥104,131 total
includes taxes & fees
Oct 27 - Oct 28
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC
Smart TV, fireplace, table tennis, computer monitors
Captain's Cottage - Cold Spring Harbor Water Views
Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (70)
"Location was perfect!"
United States
Linda J P.
The price is ￥31,795
￥73,176 total
includes taxes & fees
Nov 4 - Nov 5
Captain's Cottage - Cold Spring Harbor Water Views
Fridge, oven, stovetop, coffee/tea maker
Centric property close to all the great things in the city
Centric property close to all the great things in the city
7.2 out of 10, Good, (13)
"This rental was great accommodation"
United States
Alma B.
The price is ￥24,033
￥45,377 total
includes taxes & fees
Oct 26 - Oct 27
Centric property close to all the great things in the city
Interior
Beach house in Milford, CT
Beach house in Milford, CT
10.0 out of 10, Exceptional, (1)
"Beautiful Home right on the Long Island sound, we had such a great time. Beach was easily accessible, The Host’s were amazing and went above and beyond in accommodating us. Highly recommend!!!"
United States
Alex F.
The price is ￥78,004
￥100,081 total
includes taxes & fees
Oct 29 - Oct 30
Beach house in Milford, CT
WiFi, bed sheets
Newly renovated Private bedroom near Stony Brook University
Newly renovated Private bedroom near Stony Brook University
2.0 star property
6.0 out of 10, (1)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
The price is ￥15,793
￥35,303 total
includes taxes & fees
Oct 27 - Oct 28
Newly renovated Private bedroom near Stony Brook University
On the beach, sun loungers, beach towels
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
10.0 out of 10, Exceptional, (130)
"Fantastic all around!"
United States
Risa S.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Dining
Peaceful Vintage Home with Private Lake in Redding, CT.
Peaceful Vintage Home with Private Lake in Redding, CT.
2.0 star property
10.0 out of 10, Exceptional, (1)
"Several of us stayed for one night for our kids soccer tournament. The home was spacious and had all the amenities needed to make our short stay comfortable. The host was very responsive and accommodating. "
United States
Annette H.
The price is ￥75,532
￥116,006 total
includes taxes & fees
Nov 3 - Nov 4
Peaceful Vintage Home with Private Lake in Redding, CT.
Exterior
Modern 2 Bed in BlackRock
Modern 2 Bed in BlackRock
2.0 star property
6.8 out of 10, (3)
"Cozy get away"
United States
Anonymous traveler
The price is ￥24,491
￥55,746 total
includes taxes & fees
Oct 26 - Oct 27
Modern 2 Bed in BlackRock
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
2.0 star property
10.0 out of 10, Exceptional, (10)
"IF I COULD COULD 10 STARS I WOULD, APARTMENT WAS CLEAN , EVERYTHING WORKED PROPERLY, WAS A PLEASURE"
United States
Thomas
The price is ￥18,540
￥27,285 total
includes taxes & fees
Oct 27 - Oct 28
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Interior
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches
6.0 out of 10, (2)
"Very comfortable and welcoming Only problem was only one bathroom door closed the other one appeared to be in disrepair Other then that all was well"
United States
Kathleen
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches
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

DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford

10/10 Excellent
"Very accommodating, clean and modern"
Cliff 1-night trip
Posted 17 hours ago
DoubleTree by Hilton Stamford

Find out more about Westport

Search for holiday rentals in Westport on Expedia! You can easily find your home rentals, villas, holiday apartments in Westport using one of the methods below:

  • View our selection of featured holiday rentals in Westport
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Look no further and take a look at our great range of rental properties in Westport!

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?

Beechmont - Perfect for Family Retreat!: Located near Westport, this vacation home rental is located near the airport and has a private balcony, a terrace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop. You can relax into your vacation with a private yard and a selection of games.

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 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.