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Westport Holiday Rentals

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Holiday Rentals in Westport

Sweet Studio w/ Lounge & Pool Table

10.0 out of 10, Exceptional, (3)
"All good. Great neighborhood location "
The price is AU$535
includes taxes & fees
11 Aug - 12 Aug
Sweet Studio w/ Lounge & Pool Table

Stamford Suites

4.0 star property
5.6 out of 10, (48)
"It was great relaxing stay"
The price is AU$257
includes taxes & fees
14 Aug - 15 Aug
Stamford Suites

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (63)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach

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 "
The price is AU$392
includes taxes & fees
25 Aug - 26 Aug
Guesthouse at Norwalk Inn

Business or Weekend escape

9.2 out of 10, Wonderful, (43)
"Very nice owner with great communication. "
The price is AU$229
includes taxes & fees
10 Aug - 11 Aug
Business or Weekend escape

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

9.0 out of 10, Wonderful, (7)
"This property is well maintained. Some amenities available that made our stay more enjoyable. My only issue was the amount of noise you could hear throughout the night.but once you're asleep it doesn't matter. "
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (5)
The price is AU$1,094
includes taxes & fees
11 Aug - 12 Aug
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (16)
"The covered parking was really helpful on a cold day."
Luxury Apartments by Hyatus at The Asher

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

10.0 out of 10, Exceptional, (1)
"Lovely studio in downtown...despite being downtown. Owner was very receptive Studio had everything we needed such as sundry items...coffee pods, sugar, salt pepper and earplugs...to drown out the load seagulls. Short walk to the Ampitheater. Classic art deco buildings along the walk and quite few decent restaurants"
The price is AU$362
includes taxes & fees
11 Aug - 12 Aug
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow

9.0 out of 10, Wonderful, (7)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow

Modern House in Black Rock

2.0 star property
9.0 out of 10, Wonderful, (6)
"Very easy stay and great location convenient to Fairfield University . Plenty of options to walk to for coffee or meals. Had everything we needed. Clean, well equipped. Great communication with owners. "
Modern House in Black Rock

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (65)
"Great home to stay. Beautiful area to explore!"
The price is AU$867
includes taxes & fees
6 Aug - 7 Aug
Captain's Cottage - Cold Spring Harbor Water Views

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (63)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Spacious One Bedroom suite

8.0 out of 10, Very good, (7)
"Nice stay enjoyed it "
Spacious One Bedroom suite

1856 Trading House close to water

9.4 out of 10, Exceptional, (17)
"Close to port Jefferson!"
1856 Trading House close to water

Charming 3-bedroom Beach House

Charming 3-bedroom Beach House

Stareway to Heaven Su

10.0 out of 10, Exceptional, (6)
Stareway to Heaven Su

42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

8.6 out of 10, Excellent, (7)
"I rented this place because of the location and convenience to the many things we enjoy about Milford CT. The master bedroom is top-notch as well as the living space downstairs. We hoped to use the outdoor fire place make smores, but due to a medical emergency our trip was cut short. Regardless, we enjoyed our stay at 42 Wood Ave. Thank you, Tiffany, for supplying an awesome rental."
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

10.0 out of 10, Exceptional, (1)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
The price is AU$2,147
includes taxes & fees
6 Aug - 7 Aug
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

Soothing Carriage House with Hot Tub in charming Stratford

10.0 out of 10, Exceptional, (1)
"John was a wonderful Host.We had a very relaxing time in the Hot Tub and the carriage house had everything we needed for our stay.We will definitely book again,Lisa and Holly"
Soothing Carriage House with Hot Tub in charming Stratford
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

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?

Business or Weekend escape: This holiday home rental outside of Westport is equipped with a BBQ, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker.

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 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 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.