Vacation rentals near Thomas Family Winery
We found 100 vacation rentals — enter your dates for availability
Choose the right private vacation rental that's near Thomas Family Winery. Vacation homes offer the amenities you expect for your stay with friends, family, or just your pet, like WiFi and cable TV. At the end of the day, you're sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.
Vacation rentals with weekly discounts - Thomas Family Winery
Showing deals for:Nov 7 - Nov 14
Image gallery for Cozy Cabin Madison Indiana
1010 out of 10 rating
Exceptional
(16 reviews)
Cozy Cabin Madison Indiana
Milton, KY
10% off
Price is CA $236
CA $236
CA $2,137 total
CA $2,137 total
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
15% off
Price is CA $158
CA $158
CA $1,559 total
CA $1,559 total
includes taxes & fees
Image gallery for The Artist’s A-Frame
1010 out of 10 rating
Exceptional
(14 reviews)
The Artist’s A-Frame
Madison, Indiana
10% off
Price is CA $171
CA $171
CA $1,647 total
CA $1,647 total
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
15% off
Price is CA $211
CA $211
CA $1,967 total
CA $1,967 total
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
10% off
Price is CA $214
CA $214
CA $2,055 total
CA $2,055 total
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
10% off
Price is CA $260
CA $260
CA $2,550 total
CA $2,550 total
includes taxes & fees
Image gallery for Hardy lake house. Ideal for relax fishing and spending quality time on lake.
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Hardy lake house. Ideal for relax fishing and spending quality time on lake.
Deputy, IN
20% off
Price is CA $132
CA $132
CA $1,471 total
CA $1,471 total
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
15% off
Price is CA $174
CA $174
CA $1,573 total
CA $1,573 total
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
10% off
Price is CA $394
CA $394
CA $3,734 total
CA $3,734 total
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
20% off
Price is CA $123
CA $123
CA $1,184 total
CA $1,184 total
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
10% off
Price is CA $244
CA $244
CA $2,313 total
CA $2,313 total
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
10% off
Price is CA $193
CA $193
CA $1,828 total
CA $1,828 total
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
10% off
Price is CA $185
CA $185
CA $1,799 total
CA $1,799 total
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
30% off
Price is CA $125
CA $125
CA $1,252 total
CA $1,252 total
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
10% off
Price is CA $372
CA $372
CA $3,410 total
CA $3,410 total
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
10% off
Price is CA $226
CA $226
CA $2,204 total
CA $2,204 total
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
10% off
Price is CA $178
CA $178
CA $1,705 total
CA $1,705 total
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
(193 reviews)
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Madison, IN
10% off
Price is CA $164
CA $164
CA $1,482 total
CA $1,482 total
includes taxes & fees
Image gallery for Red comfy cottage
1010 out of 10 rating
Exceptional
(74 reviews)
Red comfy cottage
Madison, IN
15% off
Price is CA $217
CA $217
CA $2,043 total
CA $2,043 total
includes taxes & fees
Image gallery for Spacious Loft/Spa in Heart of Historic Madison.
9.69.6 out of 10 rating
Exceptional
(47 reviews)
Spacious Loft/Spa in Heart of Historic Madison.
Madison, IN
10% off
Price is CA $134
CA $134
CA $1,278 total
CA $1,278 total
includes taxes & fees
Image gallery for Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
9.89.8 out of 10 rating
Exceptional
(35 reviews)
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison, IN
15% off
Price is CA $160
CA $160
CA $1,560 total
CA $1,560 total
includes taxes & fees
Image gallery for Bungalow on Main!!
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Bungalow on Main!!
Madison, IN
10% off
Price is CA $243
CA $243
CA $2,359 total
CA $2,359 total
includes taxes & fees
Find spaces that suit your style
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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)
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)
"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)
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, yards and more
More for lessMore space, more privacy, more amenities — more value