Holiday rentals near Westport Country Playhouse
We found 773 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:15 Aug - 22 Aug
Image gallery for Direct Waterfront "The Palms" Beach House
1010 out of 10 rating
Exceptional
(7 reviews)
Direct Waterfront "The Palms" Beach House
Milford, CT
8% off
Price is AU$13,098
AU$13,098
AU$1,871 per night
includes taxes & fees
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 AU$9,279
AU$9,279
AU$1,326 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 AU$2,704
AU$2,704
AU$386 per night
includes taxes & fees
Image gallery for Rowayton House Close To Town
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Rowayton House Close To Town
Norwalk, CT
8% off
Price is AU$11,573
AU$11,573
AU$1,653 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 AU$6,243
AU$6,243
AU$892 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 AU$9,249
AU$9,249
AU$1,321 per night
includes taxes & fees
Image gallery for Quaint duplex with private yard. Walk to beach, dining, & shopping!
1010 out of 10 rating
Exceptional
(40 reviews)
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Greenwich, CT
8% off
Price is AU$4,555
AU$4,555
AU$651 per night
includes taxes & fees
Image gallery for My favorite place!
9.49.4 out of 10 rating
Exceptional
(6 reviews)
My favorite place!
Danbury, CT
8% off
Price is AU$10,770
AU$10,770
AU$1,539 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 AU$2,254
AU$2,254
AU$322 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 AU$6,424
AU$6,424
AU$918 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
(16 reviews)
Second floor cottage apartment located in a private community.
Stamford, CT
8% off
Price is AU$3,211
AU$3,211
AU$459 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
5% off
Price is AU$5,658
AU$5,658
AU$808 per night
includes taxes & fees
Image gallery for Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
1010 out of 10 rating
Exceptional
(6 reviews)
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Bethel, CT
8% off
Price is AU$3,162
AU$3,162
AU$452 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 AU$1,793
AU$1,793
AU$256 per night
includes taxes & fees
Image gallery for Historic Designer City Getaway
1010 out of 10 rating
Exceptional
(8 reviews)
Historic Designer City Getaway
Easton, CT
8% off
Price is AU$11,303
AU$11,303
AU$1,615 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 AU$3,315
AU$3,315
AU$474 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 AU$10,009
AU$10,009
AU$1,430 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 AU$18,073
AU$18,073
AU$2,582 per night
includes taxes & fees
Image gallery for Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
1010 out of 10 rating
Exceptional
(29 reviews)
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
Fairfield, CT
8% off
Price is AU$6,102
AU$6,102
AU$872 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 AU$3,184
AU$3,184
AU$455 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 AU$4,324
AU$4,324
AU$618 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 AU$4,358
AU$4,358
AU$623 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 AU$6,367
AU$6,367
AU$910 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 AU$885
AU$885
AU$126 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
36 reviews(36 reviews)
DUNE Fairfield Beach
Sleeps 2 · 1 bedroom
8.88.8 out of 10
Excellentexcellent
53 reviews(53 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)
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)
Your perfect Westport getaway is here!
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
Top rated rentals - Westport Country Playhouse
Spacious and clean house.
1010 out of 10
Exceptionalexceptional
40 reviews(40 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