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Westport Holiday Rentals

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Holiday Rentals in Westport

Westport Paradise With Every Amenity!

10.0 out of 10, Exceptional, (23)
"We had such a nice stay at Mark and Sarah’s. Check in was so easy and they were very attentive to anything we needed. The property and apartment are beautiful, it was so nice waking up and seeing all the trees and it was so quiet. We will definitely be back and stay when we are visiting our daughter at Fairfield."
The price is AU$1,162
includes taxes & fees
16 Jan - 17 Jan
Westport Paradise With Every Amenity!

Studio OSM · Sunny Westport Studio Apt. Above Historic Mill

10.0 out of 10, Exceptional, (68)
"We arrived later than the posted check in and Gerard and we spoke on the phone and everything went well. We felt like we were home. The apartment is all that it said in the ad were very accurate. Quaint, cozy and no hotel hassle. The next time we visit we will definitely look for this place!"
Studio OSM · Sunny Westport Studio Apt. Above Historic Mill

Stay 3 Nights or Longer Until January 31 and Get 15% Off

10.0 out of 10, Exceptional, (3)
"After a rough year we were able to get a few days away and at the last minute chose this location. Everything we were looking for was there. The home and grounds were beautiful. The location in Westport was exactly what we wanted: magnificent fall foliage, quiet where the home was but close enough to walk to town and enjoy every aspect of being close by the town for lovely cafes and restaurants. Also, beautiful places were accessible by car in minutes such as Earthplace for trails and nature...
Stay 3 Nights or Longer Until January 31 and Get 15% Off

Stamford Suites

3.0 star property
6.8 out of 10, (773)
"It was in walking distance of the event we were going to."
The price is AU$377
includes taxes & fees
17 Jan - 18 Jan
Stamford Suites

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (46)
"Place was clean and comfortable. Some nights were louder than others with by passers from the bar next door. Otherwise pleasant visit. Could not get in the first night. Needed to get another hotel stay. Was not able to reach anyone."
The price is AU$513
includes taxes & fees
23 Jan - 24 Jan
DUNE Fairfield Beach

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AU$221
includes taxes & fees
19 Jan - 20 Jan
Business or Weekend escape

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (116)
"Enjoyed the theater room and the comfortable bed"
Lower Lvl Private 2BR/1BA Family/Pet Friendly

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

9.6 out of 10, Exceptional, (17)
"Great little spot. Central enough to get everywhere we needed to. Walked to restaurants and to a concert (about 30 minutes). Host had some treats for us when we checked in. Apartment was clean and spacious. Felt comfortable walking around the neighborhood "
The price is AU$689
includes taxes & fees
18 Jan - 19 Jan
Luxury Designer 2 bedroom+office/3bed vacation home.

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (26)
"Wonderful little bungalow. Owners are really nice and responsive. House is well maintained, cleaned and better stocked than any other rental we've been in. Thank you!!"
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"Great space would be better if there were kuerig cups to go with the machine in the kitchen"
The price is AU$518
includes taxes & fees
26 Jan - 27 Jan
Guesthouse at Norwalk Inn

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (25)
"Great communication and accommodations from the host. We were in town for a concert and the location couldn't have been better! Would recommend this stay for anyone looking within the area."
Cheerful 4 bedrooms residential house.

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

8.6 out of 10, Excellent, (4)
"The location of Ms. Jay's place is unbeatable! My group and I were in town for an event in the Total Mortgage Arena. The drive was 5 minutes max! Ms. Jay is great with communication. She was always available for any questions. The apartment is very homey, cozy and comfortable. Very nicely decorated and it has everything you might need. (We would just recommend some mirrors in the bedrooms). The place is next to a very busy street which there is always a lot of noise, especially at night. One...
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

9.8 out of 10, Exceptional, (17)
"This place was super clean and exactly as described. "
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

The Safe House - High Tech Apt #3 - 4 beds

9.8 out of 10, Exceptional, (43)
"Property worked out great for us"
The price is AU$333
includes taxes & fees
15 Jan - 16 Jan
The Safe House - High Tech Apt #3 - 4 beds

Beachfront 3-bedroom vacation home just 14 minutes from Yale University

10.0 out of 10, Exceptional, (29)
"Very comfortable home. Perfect for our grown family. We enjoyed the relaxed atmosphere, the beach and water views right outside the back steps. We set up our umbrellas and chairs, had fun using the kyack and paddle board. It was a wonderful and relaxing time together! Looking forward to it again next year."
Beachfront 3-bedroom vacation home just 14 minutes from Yale University

The Safe House - High Tech Apt #2 - 3 Beds

9.6 out of 10, Exceptional, (35)
"Enjoyed my second stay at the Safe House. Plenty of space, great proximity to Greenwich downtown."
The price is AU$333
includes taxes & fees
16 Jan - 17 Jan
The Safe House - High Tech Apt #2 - 3 Beds

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (53)
"Cute, well-appointed house, great communication, fun stay!"
The price is AU$655
includes taxes & fees
13 Jan - 14 Jan
Captain's Cottage - Cold Spring Harbor Water Views

Wow Waterfront Sunset Oasis Beach Cottage Village Winery Brewery East End NYC Hr

9.0 out of 10, Wonderful, (7)
"Very cute cottage on the water with a deck and beautiful views. A short walk into town to shops and restaurants. "
The price is AU$543
includes taxes & fees
12 Jan - 13 Jan
Wow Waterfront Sunset Oasis Beach Cottage Village Winery Brewery East End NYC Hr

Life is Better at the Beach!

10.0 out of 10, Exceptional, (28)
"When I walked in I immediately noticed how spotless the place was. Every room looked exactly like the pictures that were listed. They had all of the essentials. We didn't need anything except food. The host and the people in the neighborhood were friendly. It was a comfortable and fun stay."
Life is Better at the Beach!

Amazing Beachfront - Dog Friendly-sorry, no cats-Classic Beach House

Amazing Beachfront - Dog Friendly-sorry, no cats-Classic Beach House
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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Other types of properties in Westport you may be interested in

Inn at Longshore

2.5 star property
9.2 out of 10, Wonderful, (137)
"Beautiful Inn"
Inn at Longshore

Westport Paradise With Every Amenity!

10.0 out of 10, Exceptional, (23)
"We had such a nice stay at Mark and Sarah’s. Check in was so easy and they were very attentive to anything we needed. The property and apartment are beautiful, it was so nice waking up and seeing all the trees and it was so quiet. We will definitely be back and stay when we are visiting our daughter at Fairfield."
The price is AU$1,162
includes taxes & fees
16 Jan - 17 Jan
Westport Paradise With Every Amenity!

EVEN Hotel Norwalk, an IHG Hotel

3.5 star property
8.2 out of 10, Very good, (1008)
"Staff was super helpful my son is disabled and I needed some changes and staff did all they could to help"
The price is AU$190
includes taxes & fees
26 Jan - 27 Jan
EVEN Hotel Norwalk, an IHG Hotel
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.

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?

Lower Lvl Private 2BR/1BA Family/Pet Friendly: This holiday home rental outside of Westport offers a patio, a terrace and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals will I find in Westport?

Expedia has 50 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. Westport Country Playhouse and Levitt Pavilion 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.