Holiday rentals near Connecticut Valley Winery
We found 434 holiday rentals — enter your dates for availability
Take a look at holiday rentals near Connecticut Valley Winery that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the amenities that you expect for your stay, which might include a garden and pool. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Connecticut Valley Winery
Showing deals for:15 Aug - 22 Aug
Image gallery for Sweetbrier Farm -- Gorgeous Views, Beautiful Home
1010 out of 10 rating
Exceptional
(27 reviews)
Sweetbrier Farm -- Gorgeous Views, Beautiful Home
Litchfield, CT
12% off
Price is NZ$9,747
NZ$9,747
NZ$1,392 per night
includes taxes & fees
Image gallery for Bantam Beauty - Surrounded By Nature!
1010 out of 10 rating
Exceptional
(11 reviews)
Bantam Beauty - Surrounded By Nature!
Bantam, CT
9% off
Price is NZ$9,996
NZ$9,996
NZ$1,428 per night
includes taxes & fees
Image gallery for Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
1010 out of 10 rating
Exceptional
(9 reviews)
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Watertown, CT
8% off
Price is NZ$17,084
NZ$17,084
NZ$2,441 per night
includes taxes & fees
Image gallery for Newly renovated charming home , Brand new chefs kitchen very comfortable home .
1010 out of 10 rating
Exceptional
(8 reviews)
Newly renovated charming home , Brand new chefs kitchen very comfortable home .
Lakeville, CT
12% off
Price is NZ$4,872
NZ$4,872
NZ$696 per night
includes taxes & fees
Image gallery for Charming 3BR Hilltop House, Newly Remodeled with Arcade
1010 out of 10 rating
Exceptional
(19 reviews)
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Terryville, CT
7% off
Price is NZ$2,744
NZ$2,744
NZ$392 per night
includes taxes & fees
Image gallery for 1770 Colonial 5 Bedrooms 4 1/2 Baths Sleeps 9
1010 out of 10 rating
Exceptional
(11 reviews)
1770 Colonial 5 Bedrooms 4 1/2 Baths Sleeps 9
Litchfield, CT
25% off
Price is NZ$5,437
NZ$5,437
NZ$777 per night
includes taxes & fees
Image gallery for Long Meadow Manor, skiing, game room, Apple picking and Lake nearby
1010 out of 10 rating
Exceptional
(13 reviews)
Long Meadow Manor, skiing, game room, Apple picking and Lake nearby
Bethlehem, CT
8% off
Price is NZ$9,103
NZ$9,103
NZ$1,300 per night
includes taxes & fees
Image gallery for Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
1010 out of 10 rating
Exceptional
(32 reviews)
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Plymouth, CT
8% off
Price is NZ$6,810
NZ$6,810
NZ$973 per night
includes taxes & fees
Image gallery for Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
Cornwall Bridge, CT
8% off
Price is NZ$9,268
NZ$9,268
NZ$1,324 per night
includes taxes & fees
Image gallery for Beautiful brook-side log cabin on 3 private acres - 2 bed, 1.5 bath, entire home
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful brook-side log cabin on 3 private acres - 2 bed, 1.5 bath, entire home
Harwinton, CT
7% off
Price is NZ$3,253
NZ$3,253
NZ$465 per night
includes taxes & fees
Image gallery for Charming Cottage in Washington Depot
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Charming Cottage in Washington Depot
Washington Depot, CT
8% off
Price is NZ$4,798
NZ$4,798
NZ$685 per night
includes taxes & fees
Image gallery for Romantic and Secluded Berkshire's Gem
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Romantic and Secluded Berkshire's Gem
New Marlborough, MA
8% off
Price is NZ$8,515
NZ$8,515
NZ$1,216 per night
includes taxes & fees
Image gallery for Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
1010 out of 10 rating
Exceptional
(56 reviews)
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Canton, CT
8% off
Price is NZ$4,209
NZ$4,209
NZ$601 per night
includes taxes & fees
Image gallery for River Overlook - Check the view from your deck!
1010 out of 10 rating
Exceptional
(15 reviews)
River Overlook - Check the view from your deck!
Canton, CT
8% off
Price is NZ$2,483
NZ$2,483
NZ$355 per night
includes taxes & fees
Image gallery for The Overlook near South Farms in Litchfield County is Hospitality, integrated.
9.29.2 out of 10 rating
Wonderful
(5 reviews)
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris, CT
8% off
Price is NZ$2,871
NZ$2,871
NZ$410 per night
includes taxes & fees
Image gallery for Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sandisfield, MA
8% off
Price is NZ$2,728
NZ$2,728
NZ$390 per night
includes taxes & fees
Image gallery for Charming apartment 7 minute walk to downtown
1010 out of 10 rating
Exceptional
(11 reviews)
Charming apartment 7 minute walk to downtown
Torrington, CT
8% off
Price is NZ$2,167
NZ$2,167
NZ$310 per night
includes taxes & fees
Image gallery for Exquisite Downtown Loft Apartment
8.68.6 out of 10 rating
Excellent
(8 reviews)
Exquisite Downtown Loft Apartment
Hartford, CT
7% off
Price is NZ$2,308
NZ$2,308
NZ$330 per night
includes taxes & fees
Image gallery for Romantic weekend getaway for two! featuring a fireplace and hot tub,
9.89.8 out of 10 rating
Exceptional
(56 reviews)
Romantic weekend getaway for two! featuring a fireplace and hot tub,
Sandisfield, MA
8% off
Price is NZ$3,566
NZ$3,566
NZ$509 per night
includes taxes & fees
Image gallery for TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX
9.89.8 out of 10 rating
Exceptional
(19 reviews)
TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX
Bristol, CT
12% off
Price is NZ$2,142
NZ$2,142
NZ$306 per night
includes taxes & fees
Image gallery for Charming 2-bedroom house centrally located in Bristol
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Charming 2-bedroom house centrally located in Bristol
Bristol, CT
8% off
Price is NZ$2,014
NZ$2,014
NZ$288 per night
includes taxes & fees
Image gallery for Cozy & Chic Cabin by the Lake, with access to private Beach!
1010 out of 10 rating
Exceptional
(23 reviews)
Cozy & Chic Cabin by the Lake, with access to private Beach!
Bethlehem, CT
8% off
Price is NZ$3,605
NZ$3,605
NZ$515 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Connecticut Valley Winery
Charming Ranch Home, Backyard Sanctuary, GameRoom, Convenient to Town Center
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
105 reviews(105 reviews)
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Sleeps 8 · 2 bedrooms · 1 bathroom
The Jefferson Guest House, Spacious, Special Views
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Picturesque Lake House with 6 bedroom, 4 bath in Granby CT.
Sleeps 8 · 7 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Tranquil Litchfield Connecticut Retreat".
Sleeps 5 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
12 reviews(12 reviews)
Romantic and Secluded Berkshire's Gem
Sleeps 12 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
14 reviews(14 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