Holiday rentals near Westport Country Playhouse
We found 784 holiday rentals — enter your dates for availability
Take a look at private holiday rentals within easy reach of Westport Country Playhouse that can be your home away from home. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you need and want for your stay, which might include parking and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Westport Country Playhouse
Showing deals for:26 Dec - 2 Jan
Image gallery for Renovated Milford Beach home by Charles Island/Silver Sands Pk
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Milford, CT
8% off
Price is NZ$4,307
for 7 nights, 1 cottage
NZ$615 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Westport Country Playhouse
ESCAPE to Westport Direct WATERFRONT Beachouse w/Rooftop Deck
Sleeps 4 · 2 bedrooms · 2 bathrooms
Top rated rentals - Westport Country Playhouse
In town to check out Fairfield University
10 out of 10
exceptional
(9 reviews)
We were looking to book a shorter week in Fairfield to check out the university. This property allowed a shorter stay, which was extremely convenient for us. The location was a short drive to the university and within walking distance to the beach. The house itself was absolutely gorgeous. All levels were tastefully decorated, the house was clean, well lit, and included all modern amenities. The hosts were very attentive to our needs and responded in a timely manner. I would not hesitate to stay here again. One of the most beautiful properties I’ve ever stayed at near the beach.
Coleen C.
Stayed Jul 2025
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value