Westport Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Westport holiday rentals

Fridge, microwave, oven, stovetop

Apartment in West End - West Side

Renovated 2BR Retreat / Modern Comforts Included
10.0 out of 10, Exceptional, (2 reviews)
"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$825
HK$2,181 total
includes taxes & fees
21 Jan - 22 Jan
Renovated 2BR Retreat / Modern Comforts Included
Iron/ironing board, free WiFi, bed sheets

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (78 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Interior

Apartment in Milford

Beach Apartment in Woodmont Milford
2.0 star property
9.0 out of 10, Wonderful, (2 reviews)
"Had a great stay!"
United States
Garry G.
The price is HK$1,014
HK$2,994 total
includes taxes & fees
3 Feb - 4 Feb
Beach Apartment in Woodmont Milford
Interior

Apartment in Downtown Bridgeport

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
10.0 out of 10, Exceptional, (4 reviews)
"Nice little spot with a great host."
United States
J M.
The price is HK$943
HK$1,607 total
includes taxes & fees
26 Jan - 27 Jan
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
1 bedroom, iron/ironing board, free WiFi, bed sheets

Holiday Home in Shelton

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
9.0 out of 10, Wonderful, (2 reviews)
"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$936
HK$1,519 total
includes taxes & fees
17 Feb - 18 Feb
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Interior

Apartment in Brooklawn - St. Vincent

Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (22 reviews)
"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$981
HK$3,046 total
includes taxes & fees
21 Jan - 22 Jan
Luxury Designer 2 bedroom+office/3bed vacation home.
Terrace/patio

Apartment in Tunxis Hill

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
10.0 out of 10, Exceptional, (1 review)
"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$968
HK$2,462 total
includes taxes & fees
1 Feb - 2 Feb
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Exterior

Apartment in Kings Park

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
2.0 star property
10.0 out of 10, Exceptional, (17 reviews)
"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$969
HK$1,419 total
includes taxes & fees
28 Jan - 29 Jan
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Property grounds

Holiday Home in Greenwich

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
9.6 out of 10, Exceptional, (25 reviews)
"Very kind host very comfortable rooms"
United States
brendan o.
The price is HK$1,046
HK$2,138 total
includes taxes & fees
2 Feb - 3 Feb
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
2 bedrooms, iron/ironing board, travel cot, WiFi

Apartment in Brooklawn - St. Vincent

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
8.0 out of 10, Very good, (1 review)
"It was clean "
United States
Burton
The price is HK$825
HK$2,251 total
includes taxes & fees
21 Jan - 22 Jan
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Fridge, microwave, oven, stovetop

Apartment in West End - West Side

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful "
United States
Nolufefe Z.
The price is HK$968
HK$2,657 total
includes taxes & fees
21 Jan - 22 Jan
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
Pool

Holiday Home in Stratford

Business or Weekend escape
9.2 out of 10, Wonderful, (52 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is HK$663
HK$1,142 total
includes taxes & fees
1 Feb - 2 Feb
Business or Weekend escape
Beach

Holiday Home in Fairfield

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
10.0 out of 10, Exceptional, (24 reviews)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is HK$1,403
HK$3,783 total
includes taxes & fees
21 Jan - 22 Jan
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Dining

Holiday Home in Fairfield

Bright Escape, Top-Rated Design, Fire pit, Near Beach
10.0 out of 10, Exceptional, (11 reviews)
"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$1,357
HK$3,607 total
includes taxes & fees
21 Jan - 22 Jan
Bright Escape, Top-Rated Design, Fire pit, Near Beach
TV, offices

Apartment in Milford

Beach Apartment in Woodmont Milford 102
2.0 star property
The price is HK$920
HK$2,840 total
includes taxes & fees
21 Jan - 22 Jan
Beach Apartment in Woodmont Milford 102
Fridge, microwave, oven, stovetop

Holiday Home in North End

Marine Theme - 4 BR - Backyard - Fire pit
9.8 out of 10, Exceptional, (8 reviews)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
The price is HK$1,305
HK$3,293 total
includes taxes & fees
2 Feb - 3 Feb
Marine Theme - 4 BR - Backyard - Fire pit
Marina

Holiday Home in Cold Spring Harbor

Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (74 reviews)
"We loved this little cottage. It was very clean and organized and the location was great!! It was nice to have space to relax and not be stuck in a small hotel room. "
United States
Laurie M.
The price is HK$1,575
HK$3,634 total
includes taxes & fees
21 Jan - 22 Jan
Captain's Cottage - Cold Spring Harbor Water Views
Dining

Holiday Home in Historic District

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
2.0 star property
10.0 out of 10, Exceptional, (9 reviews)
"Stayed with our adult children for a family wedding. Everyone enjoyed the spotless, attractive & appointed home with lovely king beds in all the rooms. It was a treat!Host was very attentive, would highly recommend!"
United States
Nancy B.
The price is HK$1,481
HK$3,772 total
includes taxes & fees
5 Feb - 6 Feb
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Property grounds

Holiday Home in Waterside

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,228
HK$2,566 total
includes taxes & fees
22 Jan - 23 Jan
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
1 bedroom, iron/ironing board, free WiFi, bed sheets

Apartment in Huntington Station

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
10.0 out of 10, Exceptional, (7 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is HK$1,520
HK$2,993 total
includes taxes & fees
24 Jan - 25 Jan
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
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

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

10/10 Excellent
"All good."
Jack 1-night trip
Posted 5 days ago
Hyatt Place Milford / New Haven

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.