Holiday rentals near Ridgefield Playhouse
We found 785 holiday rentals — enter your dates for availability
Choose the right holiday rental within close proximity to Ridgefield Playhouse. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as a garden and pool. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Ridgefield Playhouse
Showing deals for:7 Nov - 14 Nov
Image gallery for Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups
Brookfield, CT
17% off
Price is AU$19,536
AU$19,536
AU$2,791 per night
includes taxes & fees
Image gallery for Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball
1010 out of 10 rating
Exceptional
(5 reviews)
Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball
New Fairfield, CT
8% off
Price is AU$4,677
AU$4,677
AU$668 per night
includes taxes & fees
Image gallery for Candlewood Lake Perfection: Large and very private House, property and pool.
1010 out of 10 rating
Exceptional
(18 reviews)
Candlewood Lake Perfection: Large and very private House, property and pool.
Danbury, CT
8% off
Price is AU$24,206
AU$24,206
AU$3,458 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
(18 reviews)
Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!
Fairfield, CT
8% off
Price is AU$18,478
AU$18,478
AU$2,640 per night
includes taxes & fees
Image gallery for RAIN, SNOW OR SHINE! THIS HOUSE HAS ALL YOU NEED AND MORE TO HAVE A GOOD TIME !
1010 out of 10 rating
Exceptional
(5 reviews)
RAIN, SNOW OR SHINE! THIS HOUSE HAS ALL YOU NEED AND MORE TO HAVE A GOOD TIME !
Pound Ridge, NY
5% off
Price is AU$16,119
AU$16,119
AU$2,303 per night
includes taxes & fees
Image gallery for Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
1010 out of 10 rating
Exceptional
(79 reviews)
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
New Fairfield, CT
12% off
Price is AU$17,921
AU$17,921
AU$2,560 per night
includes taxes & fees
Image gallery for Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam
1010 out of 10 rating
Exceptional
(7 reviews)
Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam
New Fairfield, CT
8% off
Price is AU$20,346
AU$20,346
AU$2,907 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$11,558
AU$11,558
AU$1,651 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
(7 reviews)
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Bethel, CT
8% off
Price is AU$2,783
AU$2,783
AU$398 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$9,022
AU$9,022
AU$1,289 per night
includes taxes & fees
Image gallery for Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
1010 out of 10 rating
Exceptional
(25 reviews)
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Danbury, CT
8% off
Price is AU$6,135
AU$6,135
AU$876 per night
includes taxes & fees
Image gallery for Fun, Friends, and Family Lakefront Home w/Dock and Beach
1010 out of 10 rating
Exceptional
(12 reviews)
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Mahopac, NY
12% off
Price is AU$7,398
AU$7,398
AU$1,057 per night
includes taxes & fees
Image gallery for Stunning Waterfall View - 5 Bedroom
1010 out of 10 rating
Exceptional
(9 reviews)
Stunning Waterfall View - 5 Bedroom
Westport, CT
8% off
Price is AU$9,119
AU$9,119
AU$1,303 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$21,775
AU$21,775
AU$3,111 per night
includes taxes & fees
Image gallery for Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
1010 out of 10 rating
Exceptional
(15 reviews)
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Carmel, NY
19% off
Price is AU$5,422
AU$5,422
AU$775 per night
includes taxes & fees
Image gallery for Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
1010 out of 10 rating
Exceptional
(30 reviews)
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
New Fairfield, CT
8% off
Price is AU$3,864
AU$3,864
AU$552 per night
includes taxes & fees
Image gallery for Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT
Brewster, NY
8% off
Price is AU$13,541
AU$13,541
AU$1,934 per night
includes taxes & fees
Image gallery for Adorable 1-Bedroom Cottage in Weston, CT
1010 out of 10 rating
Exceptional
(42 reviews)
Adorable 1-Bedroom Cottage in Weston, CT
Weston, CT
8% off
Price is AU$2,443
AU$2,443
AU$349 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
9% off
Price is AU$5,814
AU$5,814
AU$831 per night
includes taxes & fees
Image gallery for A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
1010 out of 10 rating
Exceptional
(6 reviews)
A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
Holmes, NY
8% off
Price is AU$4,387
AU$4,387
AU$627 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$3,213
AU$3,213
AU$459 per night
includes taxes & fees
Image gallery for Cheerful 4 bedrooms residential house.
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Cheerful 4 bedrooms residential house.
Bridgeport, CT
8% off
Price is AU$3,513
AU$3,513
AU$502 per night
includes taxes & fees
Image gallery for Candlewood Cabin - with Private Waterfront
1010 out of 10 rating
Exceptional
(9 reviews)
Candlewood Cabin - with Private Waterfront
New Fairfield, CT
8% off
Price is AU$3,587
AU$3,587
AU$512 per night
includes taxes & fees
Image gallery for Ultra Secluded mountaintop mansion amazing views-hot tub-arcade
8.48.4 out of 10 rating
Very good
(18 reviews)
Ultra Secluded mountaintop mansion amazing views-hot tub-arcade
Mahopac, NY
16% off
Price is AU$9,579
AU$9,579
AU$1,368 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Ridgefield Playhouse
Charming Grand View/Lake Loft in Brewster with WiFi, AC
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
6 reviews(6 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