Holiday rentals near Thomas Family Winery
We found 99 holiday rentals — enter your dates for availability
Choose the right holiday rental that's near Thomas Family Winery. Holiday homes offer the best amenities for you and your friends, family or even pets, including parking and a garden. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Thomas Family Winery
Showing deals for:14 Nov - 21 Nov
Image gallery for Cozy Cabin Madison Indiana
1010 out of 10 rating
Exceptional
(16 reviews)
Cozy Cabin Madison Indiana
Milton, KY
8% off
Price is S$1,970
S$1,970
S$281 per night
includes taxes & fees
Image gallery for The Waterfall Suite Place + Walkout! Both Overlook Waterfall!
9.89.8 out of 10 rating
Exceptional
(41 reviews)
The Waterfall Suite Place + Walkout! Both Overlook Waterfall!
Pendleton, KY
11% off
Price is S$3,877
S$3,877
S$554 per night
includes taxes & fees
Image gallery for The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
1010 out of 10 rating
Exceptional
(26 reviews)
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Hanover, IN
11% off
Price is S$1,435
S$1,435
S$205 per night
includes taxes & fees
Image gallery for Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Madison, IN
12% off
Price is S$1,811
S$1,811
S$259 per night
includes taxes & fees
Image gallery for The Artist’s A-Frame
1010 out of 10 rating
Exceptional
(15 reviews)
The Artist’s A-Frame
Madison, IN
8% off
Price is S$1,502
S$1,502
S$215 per night
includes taxes & fees
Image gallery for The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!
1010 out of 10 rating
Exceptional
(42 reviews)
The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!
Madison, IN
8% off
Price is S$1,892
S$1,892
S$270 per night
includes taxes & fees
Image gallery for Pet friendly Nature Cottage: deck, trails, fire pit, creek, & historic district
9.89.8 out of 10 rating
Exceptional
(36 reviews)
Pet friendly Nature Cottage: deck, trails, fire pit, creek, & historic district
Madison, IN
16% off
Price is S$1,089
S$1,089
S$156 per night
includes taxes & fees
Image gallery for 3-suite cottage spa (aaaah!) house—amenities galore, in historic Madison Indiana
1010 out of 10 rating
Exceptional
(17 reviews)
3-suite cottage spa (aaaah!) house—amenities galore, in historic Madison Indiana
Madison, IN
12% off
Price is S$3,715
S$3,715
S$531 per night
includes taxes & fees
Image gallery for Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
1010 out of 10 rating
Exceptional
(7 reviews)
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Madison, IN
12% off
Price is S$1,447
S$1,447
S$207 per night
includes taxes & fees
Image gallery for Stoney Creek - Sit back and unwind
1010 out of 10 rating
Exceptional
(91 reviews)
Stoney Creek - Sit back and unwind
Madison, IN
7% off
Price is S$1,656
S$1,656
S$237 per night
includes taxes & fees
Image gallery for BEAUTIFUL MainStreet Madison Home! Walk to it ALL
1010 out of 10 rating
Exceptional
(10 reviews)
BEAUTIFUL MainStreet Madison Home! Walk to it ALL
Madison, IN
7% off
Price is S$1,648
S$1,648
S$235 per night
includes taxes & fees
Image gallery for Rustic cabin just outside of Madison!
1010 out of 10 rating
Exceptional
(41 reviews)
Rustic cabin just outside of Madison!
Madison, IN
7% off
Price is S$2,030
S$2,030
S$290 per night
includes taxes & fees
Image gallery for East Main Lofts - Boho 203
9.89.8 out of 10 rating
Exceptional
(7 reviews)
East Main Lofts - Boho 203
Madison, IN
8% off
Price is S$2,131
S$2,131
S$304 per night
includes taxes & fees
Image gallery for "Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit
9.49.4 out of 10 rating
Exceptional
(8 reviews)
"Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit
Madison, IN
7% off
Price is S$2,115
S$2,115
S$302 per night
includes taxes & fees
Image gallery for 1800’s restored log cabin on 26 private rolling wooded acres with sunset views
1010 out of 10 rating
Exceptional
(194 reviews)
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Madison, IN
8% off
Price is S$1,364
S$1,364
S$195 per night
includes taxes & fees
Image gallery for Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
1010 out of 10 rating
Exceptional
(53 reviews)
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
Madison, IN
16% off
Price is S$4,354
S$4,354
S$622 per night
includes taxes & fees
Image gallery for River Views from Every Room! Clean, Newly Remodeled, Full Kitchen
9.89.8 out of 10 rating
Exceptional
(59 reviews)
River Views from Every Room! Clean, Newly Remodeled, Full Kitchen
Madison, IN
8% off
Price is S$1,683
S$1,683
S$240 per night
includes taxes & fees
Image gallery for The Wee House is a shotgun house that is remodeled with a view of the Ohio river
9.69.6 out of 10 rating
Exceptional
(50 reviews)
The Wee House is a shotgun house that is remodeled with a view of the Ohio river
Madison, IN
23% off
Price is S$1,151
S$1,151
S$164 per night
includes taxes & fees
Image gallery for River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
9.89.8 out of 10 rating
Exceptional
(9 reviews)
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Madison, IN
8% off
Price is S$2,531
S$2,531
S$362 per night
includes taxes & fees
Image gallery for The Wadsworth in National Historic District of Madison, Indiana.
1010 out of 10 rating
Exceptional
(51 reviews)
The Wadsworth in National Historic District of Madison, Indiana.
Madison, IN
8% off
Price is S$2,230
S$2,230
S$319 per night
includes taxes & fees
Image gallery for The Nature House is a perfect mix of charm and location!
1010 out of 10 rating
Exceptional
(27 reviews)
The Nature House is a perfect mix of charm and location!
Madison, IN
8% off
Price is S$3,140
S$3,140
S$449 per night
includes taxes & fees
Image gallery for The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
1010 out of 10 rating
Exceptional
(7 reviews)
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Madison, IN
8% off
Price is S$1,420
S$1,420
S$203 per night
includes taxes & fees
Image gallery for Red comfy cottage
1010 out of 10 rating
Exceptional
(75 reviews)
Red comfy cottage
Madison, IN
12% off
Price is S$1,882
S$1,882
S$269 per night
includes taxes & fees
Image gallery for Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!
1010 out of 10 rating
Exceptional
(7 reviews)
Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!
Madison, IN
7% off
Price is S$2,008
S$2,008
S$287 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Thomas Family Winery
Spacious Loft/Spa in Heart of Historic Madison.
Sleeps 4 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
"Madison Manor II" by The River: Regatta Special! Patio-Fire Pit, Grill, Hot Tub
Sleeps 6 · 2 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Pet friendly Nature Cottage: deck, trails, fire pit, creek, & historic district
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
36 reviews(36 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