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Top Holiday Rentals in Westport

Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

The price is £1,869
includes taxes & fees
30 Jun - 1 Jul
Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

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

10.0 out of 10, Exceptional, (6)
"Property manager was very attentive to our needs and replied to all msgs in a very timely fashion. There were a couple things that needed tending to when we arrived and he took care of it immediately. Despite having parking on the street, it was never an issue and often got the spot that was right next to the house. The beach was directly across the street and was clean with friendly neighbors! Although there is a sign stating no dogs or animals allowed on the beach, there were many dogs on the...
The price is £425
includes taxes & fees
5 Jul - 6 Jul
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Beach house in Milford, CT

The price is £530
includes taxes & fees
30 Jun - 1 Jul
Beach house in Milford, CT

3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beach

10.0 out of 10, Exceptional, (1)
"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"
The price is £498
includes taxes & fees
16 Jul - 17 Jul
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beach

My little place Cozy Open concept for quiet time.

8.0 out of 10, Very good, (2)
"Great, clean property that was easy to access and very convenient to downtown Bridgeport. Perfect place to clean up and sleep. Very welcoming space."
The price is £367
includes taxes & fees
1 Jul - 2 Jul
My little place Cozy Open concept for quiet time.

Business or Weekend escape

9.6 out of 10, Exceptional, (38)
"Very nice owner with great communication. "
The price is £110
includes taxes & fees
6 Jul - 7 Jul
Business or Weekend escape

Seaview Ave House-4BR/8PPL Retreat

9.6 out of 10, Exceptional, (10)
"This was an awesome place to stay. Very clean and well kept. When I needed to get in touch for some last minute questions, the owner was very prompt and eager to help. I would definitely stay here again."
The price is £551
includes taxes & fees
2 Jul - 3 Jul
Seaview Ave House-4BR/8PPL Retreat

Amazingly Cozy Comfort Downtwn, Amphitheater, 2 min ferry & train station

10.0 out of 10, Exceptional, (1)
"Great experience. Very close to a lot of downtown restaurants and Bridgeton. 10 to 15 mnutes from the beach. Lots of added special touches and amenities. Great job by the host."
The price is £135
includes taxes & fees
7 Jul - 8 Jul
Amazingly Cozy Comfort Downtwn, Amphitheater, 2 min ferry & train station

Upscale 4BR Retreat at the Reservoir!

The price is £658
includes taxes & fees
1 Jul - 2 Jul
Upscale 4BR Retreat at the Reservoir!

Charming Long Island Family Getaway with Pool. An hour from Hamptons

7.0 out of 10, Good, (6)
"Had a great time here. The house was clean and well maintained. The host communicated with us often and overall it was a great stay!"
The price is £1,249
includes taxes & fees
20 Jul - 21 Jul
Charming Long Island Family Getaway with Pool. An hour from Hamptons

Centric property close to all the great things in the city

8.2 out of 10, Very good, (12)
"This rental was great accommodation"
The price is £225
includes taxes & fees
30 Jun - 1 Jul
Centric property close to all the great things in the city

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

The price is £1,108
includes taxes & fees
30 Jun - 1 Jul
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

Charming 2-bedroom house with WiFi, AC in Fairfield

10.0 out of 10, Exceptional, (1)
"Amalfi’s place was as described. It was clean and comfortable and mostly quiet. Amalfi was excellent with communication. Would certainly stay again when visiting family."
The price is £259
includes taxes & fees
30 Jun - 1 Jul
Charming 2-bedroom house with WiFi, AC in Fairfield

Marine Theme - 4 BR - Backyard - Fire pit

9.8 out of 10, Exceptional, (6)
"Had a great stay at Sarah’s place. She was very communicative and helpful before and during our stay. The house was nice and large - it was great having two living rooms for our large group. Convenient location close to many stores and sights!"
The price is £391
includes taxes & fees
6 Jul - 7 Jul
Marine Theme - 4 BR - Backyard - Fire pit

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

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."
The price is £142
includes taxes & fees
23 Jul - 24 Jul
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

10.0 out of 10, Exceptional, (17)
"Very comfortable home. Lots of thought in providing all needed for a stay. We so appreciated the hosts communication...made life pleasant. We will repeat!"
The price is £535
includes taxes & fees
6 Jul - 7 Jul
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Bright Escape, Top-Rated Design, Fire pit, Near Beach, 90 minutes to NYC

10.0 out of 10, Exceptional, (5)
"And the bed was confortable"
The price is £439
includes taxes & fees
1 Jul - 2 Jul
Bright Escape, Top-Rated Design, Fire pit, Near Beach, 90 minutes to NYC

Updated, cozy single family in Fairfield County

9.2 out of 10, Wonderful, (10)
"House was great, hosts were attentive. Enjoyed our stay"
The price is £340
includes taxes & fees
1 Jul - 2 Jul
Updated, cozy single family in Fairfield County

Cozy cute Relaxing home

9.0 out of 10, Wonderful, (2)
"nice quiet area"
The price is £223
includes taxes & fees
30 Jun - 1 Jul
Cozy cute Relaxing home

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

10.0 out of 10, Exceptional, (3)
"Great space! Very clean & well appointed! If you forgot to pack it, it is probably there!"
The price is £294
includes taxes & fees
30 Jun - 1 Jul
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
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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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?

Main Street Westport, walk to shops, dining, downtown: This highly rated holiday home rental in Westport is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a fridge, a microwave and a coffee maker, so that you can cook with friends or family.

How many holiday rentals will I find in Westport?

Expedia has 55 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.