Holiday rentals near Westport Country Playhouse
We found 769 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:8 Aug - 15 Aug
Image gallery for Beautiful Waterfront Sunset Beach House Oasis Walk to Village Beaches 1hr NYC
1010 out of 10 rating
Exceptional
(5 reviews)
Beautiful Waterfront Sunset Beach House Oasis Walk to Village Beaches 1hr NYC
Northport, NY
12% off
Price is NZ$10,062
NZ$10,062
NZ$1,437 per night
includes taxes & fees
Image gallery for Cozy country cottage in horse country ,private 1 hour toNYC
9.69.6 out of 10 rating
Exceptional
(28 reviews)
Cozy country cottage in horse country ,private 1 hour toNYC
South Salem, NY
8% off
Price is NZ$2,960
NZ$2,960
NZ$423 per night
includes taxes & fees
Image gallery for Mid Century Modern ZEN House with Pool. 50 min from New York City
1010 out of 10 rating
Exceptional
(19 reviews)
Mid Century Modern ZEN House with Pool. 50 min from New York City
Stamford, CT
8% off
Price is NZ$6,813
NZ$6,813
NZ$973 per night
includes taxes & fees
Image gallery for Entire home PRIVATE BEACH live like a celebrity! Saturday-Saturday ONLY
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Entire home PRIVATE BEACH live like a celebrity! Saturday-Saturday ONLY
Milford, CT
8% off
Price is NZ$10,040
NZ$10,040
NZ$1,434 per night
includes taxes & fees
Image gallery for Private 1-bedroom apartment in beautiful town of Centerport. Great amenities!
1010 out of 10 rating
Exceptional
(6 reviews)
Private 1-bedroom apartment in beautiful town of Centerport. Great amenities!
Centerport, NY
9% off
Price is NZ$2,437
NZ$2,437
NZ$348 per night
includes taxes & fees
Image gallery for 2-bedroom vacation home just 24 minutes from Yale University
9.69.6 out of 10 rating
Exceptional
(19 reviews)
2-bedroom vacation home just 24 minutes from Yale University
Shelton, CT
10% off
Price is NZ$1,846
NZ$1,846
NZ$264 per night
includes taxes & fees
Image gallery for Life is Better at the Beach!
1010 out of 10 rating
Exceptional
(28 reviews)
Life is Better at the Beach!
Milford, CT
8% off
Price is NZ$7,006
NZ$7,006
NZ$1,001 per night
includes taxes & fees
Image gallery for Second floor cottage apartment located in a private community.
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Second floor cottage apartment located in a private community.
Stamford, CT
8% off
Price is NZ$3,515
NZ$3,515
NZ$502 per night
includes taxes & fees
Image gallery for 2nd Floor, 1 Br / 1 Ba With Sofa Bed In The Living Room
9.89.8 out of 10 rating
Exceptional
(10 reviews)
2nd Floor, 1 Br / 1 Ba With Sofa Bed In The Living Room
Greenwich, CT
7% off
Price is NZ$1,927
NZ$1,927
NZ$275 per night
includes taxes & fees
Image gallery for ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
1010 out of 10 rating
Exceptional
(25 reviews)
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
Stamford, CT
6% off
Price is NZ$5,341
NZ$5,341
NZ$763 per night
includes taxes & fees
Image gallery for Luxury private beach front property
1010 out of 10 rating
Exceptional
(11 reviews)
Luxury private beach front property
Milford, CT
12% off
Price is NZ$11,337
NZ$11,337
NZ$1,620 per night
includes taxes & fees
Image gallery for Cozy, pleasant 2BR apt in Beach community! Only 1hr to NYC!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Cozy, pleasant 2BR apt in Beach community! Only 1hr to NYC!
Norwalk, CT
8% off
Price is NZ$3,677
NZ$3,677
NZ$525 per night
includes taxes & fees
Image gallery for Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
1010 out of 10 rating
Exceptional
(28 reviews)
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
Fairfield, CT
8% off
Price is NZ$6,662
NZ$6,662
NZ$952 per night
includes taxes & fees
Image gallery for Quiet suburban home close to Fairfield beaches and universities
1010 out of 10 rating
Exceptional
(8 reviews)
Quiet suburban home close to Fairfield beaches and universities
Fairfield, CT
8% off
Price is NZ$3,486
NZ$3,486
NZ$498 per night
includes taxes & fees
Image gallery for The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace
9.09.0 out of 10 rating
Wonderful
(6 reviews)
The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace
Stamford, CT
8% off
Price is NZ$8,871
NZ$8,871
NZ$1,267 per night
includes taxes & fees
Image gallery for Historic 6-Bdrm Tudor Estate w pool/tennis access
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Historic 6-Bdrm Tudor Estate w pool/tennis access
Stamford, CT
8% off
Price is NZ$20,566
NZ$20,566
NZ$2,938 per night
includes taxes & fees
Image gallery for Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC
Northport, NY
12% off
Price is NZ$4,730
NZ$4,730
NZ$676 per night
includes taxes & fees
Image gallery for Adorable Cottage with Water Views, Across the street from Prime & other eateries
9.89.8 out of 10 rating
Exceptional
(63 reviews)
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Huntington, NY
8% off
Price is NZ$4,768
NZ$4,768
NZ$681 per night
includes taxes & fees
Image gallery for Vrbo Property
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Vrbo Property
Bridgeport, CT
8% off
Price is NZ$6,947
NZ$6,947
NZ$992 per night
includes taxes & fees
Image gallery for 1 bedroom Cozy, comfy, super clean, great location and own entrance!!
9.49.4 out of 10 rating
Exceptional
(32 reviews)
1 bedroom Cozy, comfy, super clean, great location and own entrance!!
Shelton, CT
7% off
Price is NZ$975
NZ$975
NZ$139 per night
includes taxes & fees
Image gallery for New Beach Home near Stamford Downtown/Shippan
1010 out of 10 rating
Exceptional
(20 reviews)
New Beach Home near Stamford Downtown/Shippan
Stamford, Connecticut
6% off
Price is NZ$20,090
NZ$20,090
NZ$2,870 per night
includes taxes & fees
Image gallery for Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
1010 out of 10 rating
Exceptional
(21 reviews)
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Rye Brook, NY
8% off
Price is NZ$3,092
NZ$3,092
NZ$442 per night
includes taxes & fees
Image gallery for Centric property close to all the great things in the city
8.28.2 out of 10 rating
Very good
(10 reviews)
Centric property close to all the great things in the city
Bridgeport, CT
12% off
Price is NZ$2,296
NZ$2,296
NZ$328 per night
includes taxes & fees
Image gallery for Lordship Charmer HAS IT ALL! Comfortable stay, accessible, family friendly!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Lordship Charmer HAS IT ALL! Comfortable stay, accessible, family friendly!
Stratford, CT
8% off
Price is NZ$4,185
NZ$4,185
NZ$598 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Westport Country Playhouse
Business or Weekend escape
Sleeps 4 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
Cheerful 4 bedrooms residential house.
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Seaside Serenity: 2B 1B, Patio,Near Beach
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
DUNE Fairfield Beach
Sleeps 2 · 1 bedroom
8.88.8 out of 10
Excellentexcellent
52 reviews(52 reviews)
Your perfect Westport getaway is here!
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Luxury Designer 2 bedroom+office/3bed vacation home.
Sleeps 5 · 3 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
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