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Westport Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Westport holiday rentals

Fridge, microwave, oven, stovetop
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
The price is HK$824
HK$2,264 total
includes taxes & fees
11 Jan - 12 Jan
Renovated 2BR Retreat / Modern Comforts Included
Iron/ironing board, free WiFi, bed sheets
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
DUNE Fairfield Beach
Interior
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.
The price is HK$997
HK$2,964 total
includes taxes & fees
12 Jan - 13 Jan
Beach Apartment in Woodmont Milford
1 bedroom, iron/ironing board, free WiFi, bed sheets
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Shelton
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is HK$934
HK$1,532 total
includes taxes & fees
11 Jan - 12 Jan
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Exterior
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.
The price is HK$967
HK$1,417 total
includes taxes & fees
9 Jan - 10 Jan
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Terrace/patio
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.
The price is HK$967
HK$2,459 total
includes taxes & fees
29 Jan - 30 Jan
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
1 bedroom, desk, iron/ironing board, free WiFi
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

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
9.6 out of 10, Exceptional, (7)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
United States
Caroline
The price is HK$1,090
HK$1,806 total
includes taxes & fees
9 Jan - 10 Jan
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Pool
Business or Weekend escape

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is HK$662
HK$1,141 total
includes taxes & fees
1 Feb - 2 Feb
Business or Weekend escape
2 bedrooms, iron/ironing board, travel cot, WiFi
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
The price is HK$824
HK$2,264 total
includes taxes & fees
9 Jan - 10 Jan
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Dining
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.
The price is HK$1,386
HK$3,740 total
includes taxes & fees
26 Jan - 27 Jan
Bright Escape, Top-Rated Design, Fire pit, Near Beach
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.
The price is HK$999
HK$2,059 total
includes taxes & fees
12 Jan - 13 Jan
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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.
The price is HK$1,144
HK$2,873 total
includes taxes & fees
1 Feb - 2 Feb
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
Outdoor dining
🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna

🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna

🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna
Tunxis Hill
10.0 out of 10, Exceptional, (1)
"The Host was welcoming and responsive to our inquiries!Our stay was wonderful! The property was spectacular and offered all the amenities we needed for a comfortable and enjoyable visit. "
United States
Patricia B.
The price is HK$6,228
HK$15,718 total
includes taxes & fees
19 Jan - 20 Jan
🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna
Dining
Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!

Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!

Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
Milford
9.6 out of 10, Exceptional, (5)
"We recommend this house and would defintely come again. Thank you for a lovely stay."
United States
Mary Lynn S.
Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
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.
The price is HK$1,336
HK$3,349 total
includes taxes & fees
12 Jan - 13 Jan
Marine Theme - 4 BR - Backyard - Fire pit
Interior
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.
The price is HK$1,240
HK$3,357 total
includes taxes & fees
2 Feb - 3 Feb
Luxury Designer 2 bedroom+office/3bed vacation home.
Exterior
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

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, (7)
"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 HK$6,453
HK$11,831 total
includes taxes & fees
9 Jan - 10 Jan
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
Beach
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.
The price is HK$1,386
HK$3,737 total
includes taxes & fees
11 Jan - 12 Jan
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Property grounds
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

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (9)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,226
HK$2,563 total
includes taxes & fees
11 Jan - 12 Jan
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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
The price is HK$825
HK$2,713 total
includes taxes & fees
11 Jan - 12 Jan
Beach Apartment in Woodmont Milford 102
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

La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

10/10 Excellent
"Thx"
Maritza 3-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Stamford / New York City

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
  • Use the map to find apartments and other holiday homes in the Westport neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Westport while they last

Look no further and take a look at our great range of rental properties in Westport!

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Frequently asked questions

Can I find holiday rentals in Westport?

Yes, there are holiday rentals in Westport close to Earthplace Museum, or you can select a more secluded option if you're looking for a relaxing stay. Westport is known for its football games and waterfront. Make sure you have time to check out the entertainment choices and theatres during your trip.

What are some of the best holiday rentals that Westport has to offer?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of 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 holiday rentals will I find in Westport?

Expedia has 57 holiday 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 holiday rental in Westport like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Westport. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for small groups.