Holiday rentals near Westport Country Playhouse
We found 790 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:3 Oct - 10 Oct
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$3,449
AU$3,449
AU$493 per night
includes taxes & fees
Image gallery for Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!
Fairfield, CT
8% off
Price is AU$17,913
AU$17,913
AU$2,559 per night
includes taxes & fees
Image gallery for Mid-Century Modern Hilltop Retreat
9.09.0 out of 10 rating
Wonderful
(9 reviews)
Mid-Century Modern Hilltop Retreat
South Salem, NY
12% off
Price is AU$8,835
AU$8,835
AU$1,262 per night
includes taxes & fees
Image gallery for Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
1010 out of 10 rating
Exceptional
(9 reviews)
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Weston, CT
8% off
Price is AU$4,447
AU$4,447
AU$635 per night
includes taxes & fees
Image gallery for A Secluded Modern Getaway
1010 out of 10 rating
Exceptional
(7 reviews)
A Secluded Modern Getaway
Redding, CT
8% off
Price is AU$11,369
AU$11,369
AU$1,624 per night
includes taxes & fees
Image gallery for Beachfront Home- Quiet, On The Water In Milford Connecticut
1010 out of 10 rating
Exceptional
(38 reviews)
Beachfront Home- Quiet, On The Water In Milford Connecticut
Milford, CT
8% off
Price is AU$15,379
AU$15,379
AU$2,197 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$21,161
AU$21,161
AU$3,023 per night
includes taxes & fees
Image gallery for Direct Waterfront "The Palms" Beach House
1010 out of 10 rating
Exceptional
(9 reviews)
Direct Waterfront "The Palms" Beach House
Milford, CT
8% off
Price is AU$6,573
AU$6,573
AU$939 per night
includes taxes & fees
Image gallery for 3br\2ba: Quiet and Cozy Getaway in Milford
1010 out of 10 rating
Exceptional
(6 reviews)
3br\2ba: Quiet and Cozy Getaway in Milford
Milford, CT
24% off
Price is AU$2,439
AU$2,439
AU$348 per night
includes taxes & fees
Image gallery for Charming 3 Bedroom Beach Front Cottage with Fireplace
9.49.4 out of 10 rating
Exceptional
(27 reviews)
Charming 3 Bedroom Beach Front Cottage with Fireplace
Milford, CT
8% off
Price is AU$7,070
AU$7,070
AU$1,010 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 AU$10,285
AU$10,285
AU$1,469 per night
includes taxes & fees
Image gallery for Historic Designer City Getaway
1010 out of 10 rating
Exceptional
(9 reviews)
Historic Designer City Getaway
Easton, CT
8% off
Price is AU$11,391
AU$11,391
AU$1,627 per night
includes taxes & fees
Image gallery for Luxurious, Direct Oceanfront Home with Private Beach
1010 out of 10 rating
Exceptional
(15 reviews)
Luxurious, Direct Oceanfront Home with Private Beach
Milford, CT
17% off
Price is AU$16,403
AU$16,403
AU$2,343 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
8% off
Price is AU$4,812
AU$4,812
AU$687 per night
includes taxes & fees
Image gallery for Adorable 1-Bedroom Cottage in Weston, CT
1010 out of 10 rating
Exceptional
(41 reviews)
Adorable 1-Bedroom Cottage in Weston, CT
Weston, CT
8% off
Price is AU$2,429
AU$2,429
AU$347 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
20% off
Price is AU$4,467
AU$4,467
AU$638 per night
includes taxes & fees
Image gallery for BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
1010 out of 10 rating
Exceptional
(34 reviews)
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Milford, CT
7% off
Price is AU$1,903
AU$1,903
AU$272 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$6,767
AU$6,767
AU$967 per night
includes taxes & fees
Image gallery for Stylish downstairs apartment. Walk to town, train, & beach ferry!
1010 out of 10 rating
Exceptional
(20 reviews)
Stylish downstairs apartment. Walk to town, train, & beach ferry!
Greenwich, CT
8% off
Price is AU$4,359
AU$4,359
AU$623 per night
includes taxes & fees
Image gallery for The Suite at Pound Ridge
9.69.6 out of 10 rating
Exceptional
(5 reviews)
The Suite at Pound Ridge
Pound Ridge, NY
8% off
Price is AU$3,519
AU$3,519
AU$503 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
15% off
Price is AU$3,890
AU$3,890
AU$556 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
7% off
Price is AU$3,835
AU$3,835
AU$548 per night
includes taxes & fees
Image gallery for Stylish Beach Home near Stamford Downtown/Beach
1010 out of 10 rating
Exceptional
(20 reviews)
Stylish Beach Home near Stamford Downtown/Beach
Stamford, Connecticut
8% off
Price is AU$7,614
AU$7,614
AU$1,088 per night
includes taxes & fees
Image gallery for 2nd Floor, 1 Br / 1 Ba With Sofa Bed In The Living Room
1010 out of 10 rating
Exceptional
(12 reviews)
2nd Floor, 1 Br / 1 Ba With Sofa Bed In The Living Room
Greenwich, CT
7% off
Price is AU$1,763
AU$1,763
AU$252 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
9.29.2 out of 10
Wonderfulwonderful
40 reviews(40 reviews)
DUNE Fairfield Beach
Sleeps 2 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
59 reviews(59 reviews)
Luxury Designer 2 bedroom+office/3bed vacation home.
Sleeps 5 · 3 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
Stamford Suites
Sleeps 4 · 1 bedroom
5.85.8 out of 10
44 reviews(44 reviews)
Riverfront Weston Home-1 Hr to NYC.Easy access to restaurants, I-95 & Parkway
Sleeps 6 · 2 bedrooms · 1+ bathroom
6.86.8 out of 10
5 reviews(5 reviews)
Guesthouse at Norwalk Inn
Sleeps 2 · 1 bedroom
8.48.4 out of 10
Very goodvery good
39 reviews(39 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