Photo by Eric O

Holiday Homes in Madison

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Featured Holiday Homes in Madison and around

Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly
Fridge, microwave, oven, stovetop

Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly

9.8 out of 10, Exceptional, (46)
"It was amazing "
Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly
East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly
Fridge, microwave, oven, dishwasher

East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly

9.4 out of 10, Exceptional, (66)
"The house was super Duper clean and very well organized! Definitely would like to stay there again!"
East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly
Mid Century Guest House on Wooded Lot
Smart TV, fireplace, books, music library

Mid Century Guest House on Wooded Lot

10.0 out of 10, Exceptional, (41)
"Very nice and cozy. Quiet and served all our needs. We would definitely return if in the area. "
Mid Century Guest House on Wooded Lot
LUXURY WATERFRONT HOME w/PRIVATE BEACH w/BBQ PATIO
Fridge, microwave, oven, stovetop

LUXURY WATERFRONT HOME w/PRIVATE BEACH w/BBQ PATIO

9.8 out of 10, Exceptional, (56)
"The house was nice, lots of space. To get to the lake, you need to take a lot of apes, but they’re easier than most and well worth getting to the lower deck to sit in the chais and take in the views!"
LUXURY WATERFRONT HOME w/PRIVATE BEACH w/BBQ PATIO
Cozy- SPIRE, Winery Tours, GOTL, Beach
Exterior

Cozy- SPIRE, Winery Tours, GOTL, Beach

9.6 out of 10, Exceptional, (17)
"Place was vert nice and conveniently located to our wedding venue as well as lots of wineries to visit on our off day. Would definitely stay there again"
Cozy- SPIRE, Winery Tours, GOTL, Beach
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries
Fridge, microwave, oven, stovetop

Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries

9.4 out of 10, Exceptional, (222)
"We had an amazing family reunion at one of Matt Caudill's properties on Geneva-on-the-Lake. Matt was incredibly accommodating, ensuring all our needs were met. The location of the property was perfect—close to restaurants, entertainment, and everything we needed for a fun and relaxing stay. The home itself was exceptionally well-stocked, making our stay comfortable and hassle-free. Overall, we had a wonderful experience and would highly recommend Matt's property to anyone looking for a great...
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries
Great Strip Location | Lake View | Pet Friendly | A/C | Sauna| Wine Country|WiFi
Interior

Great Strip Location | Lake View | Pet Friendly | A/C | Sauna| Wine Country|WiFi

9.8 out of 10, Exceptional, (179)
"Best place ever. Great spot well maintained."
Great Strip Location | Lake View | Pet Friendly | A/C | Sauna| Wine Country|WiFi
GENEVA-ON-LAKE Center Strip - Sunsets, happy hour & morning coffee ON the lake!
Property grounds

GENEVA-ON-LAKE Center Strip - Sunsets, happy hour & morning coffee ON the lake!

9.4 out of 10, Exceptional, (60)
"The property was just as described We had a great time Thank you"
GENEVA-ON-LAKE Center Strip - Sunsets, happy hour & morning coffee ON the lake!
Center of Strip |Pet Friendly|A/C|Wi-fi & Cable|Stately Home|Steps from Winery
Exterior

Center of Strip |Pet Friendly|A/C|Wi-fi & Cable|Stately Home|Steps from Winery

9.4 out of 10, Exceptional, (222)
"Perfect fall get away. Enjoyed the strip, shopping, good food, and sitting around the fire pit with friends and dressing up in Halloween costumes and going to see the bands at the clubs. House was in a perfect location at the center of town. We did some cooking and there were plenty of pots, pans, utensils available. Would rent again."
Center of Strip |Pet Friendly|A/C|Wi-fi & Cable|Stately Home|Steps from Winery
Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country
Fridge, microwave, oven, stovetop

Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country

9.6 out of 10, Exceptional, (205)
"Perfect location, easy check in, no hiccups, enjoyed our stay for the weekend!"
Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country
Eastlake Home w/ Patio < 1 Mi to Lake Erie!
TV

Eastlake Home w/ Patio < 1 Mi to Lake Erie!

9.4 out of 10, Exceptional, (10)
"It was very peaceful. "
Eastlake Home w/ Patio < 1 Mi to Lake Erie!
Great Strip Location | Walk to Lake | Wine Country | A/C | Grill & Firepit
Terrace/patio

Great Strip Location | Walk to Lake | Wine Country | A/C | Grill & Firepit

8.4 out of 10, Very good, (49)
"Cottage was a perfect size for what we needed. Location was great. Communication was easy with the property owner. Would stay there again. "
Great Strip Location | Walk to Lake | Wine Country | A/C | Grill & Firepit
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C
Property grounds

Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C

9.4 out of 10, Exceptional, (295)
"This was the perfect landing spot for our fall wine weekend to NE Ohio. We had a great time and would recommend. "
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C
Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country
Beach nearby

Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country

9.6 out of 10, Exceptional, (176)
"Nice house withing walking distance from pretty much everything "
Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country
Great Strip Location|WalktoLake|Wine Country|AC|Grill&Firepit|FamilyFriendly
Exterior

Great Strip Location|WalktoLake|Wine Country|AC|Grill&Firepit|FamilyFriendly

9.4 out of 10, Exceptional, (79)
"Was very nice, would like to stay there again. Would like to recommend to everyone "
Great Strip Location|WalktoLake|Wine Country|AC|Grill&Firepit|FamilyFriendly
East End of The Strip. A/C Wifi Cable TV Firepit Walk to Park/Lake Wineries
Property grounds

East End of The Strip. A/C Wifi Cable TV Firepit Walk to Park/Lake Wineries

9.6 out of 10, Exceptional, (71)
"Had a great time. House was a lot bigger than I thought. Very clean."
East End of The Strip. A/C Wifi Cable TV Firepit Walk to Park/Lake Wineries
Ultimate Wine Country Retreat | Hot Tub, Arcade, and Mins to Spire and Winery!
Outdoor spa tub

Ultimate Wine Country Retreat | Hot Tub, Arcade, and Mins to Spire and Winery!

10.0 out of 10, Exceptional, (53)
"We absolutely loved the nautical themed loft and highly recommend to anyone wanting to stay in wine country! Can’t way to come back!"
Ultimate Wine Country Retreat | Hot Tub, Arcade, and Mins to Spire and Winery!
Central Location- SPIRE, Wineries, GOTL, Beach
Fridge, microwave, oven, stovetop

Central Location- SPIRE, Wineries, GOTL, Beach

9.6 out of 10, Exceptional, (19)
"The host was very responsive to questions. Great location to wineries and great food in downtown Ashtabula. Beds were comfortable and large table was great for games and cards after visiting wineries. Would definitely stay again. "
Central Location- SPIRE, Wineries, GOTL, Beach
Geauga Maple Cottage
Point of interest

Geauga Maple Cottage

10.0 out of 10, Exceptional, (168)
"A friend got married in Novelty and my choice of close places to stay were hotels East or Chagrin - I made the right choice. House is on a Main Street, but it is quiet, I didn’t hear a thing either night of our stay. Owners next door and friendly. There is a bar 100 yards away which I didn’t hear a peep from. I would stay again. If you want to have cable you need to bring a fire stick or other plug in device for the tv. "
Geauga Maple Cottage
Lakeview Ashtabula, OH - 5 min to GOTL - Deck - King - Wineries - Lake Erie
Beach/ocean view

Lakeview Ashtabula, OH - 5 min to GOTL - Deck - King - Wineries - Lake Erie

10.0 out of 10, Exceptional, (12)
"Sunset and waking up on the lake. Need I say more. 😍"
The price is €484
includes taxes & fees
24 Nov - 25 Nov
Lakeview Ashtabula, OH - 5 min to GOTL - Deck - King - Wineries - Lake Erie
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Madison

Lakefront Property, Family Friendly and Pets Allowed
Terrace/patio

Lakefront Property, Family Friendly and Pets Allowed

9.8 out of 10, Exceptional, (101)
"This was our 2nd stay at this property. The house was immaculate. Absolutely the cleanest house we’ve rented. The view is magnificent. We had terrific weather so we utilized the spacious patios to enjoy wine and sun sets. New from last year is the Vincent William winery/restaurant that’s a short walk. Great food"
Lakefront Property, Family Friendly and Pets Allowed
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries
Fridge, microwave, oven, stovetop

Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries

9.4 out of 10, Exceptional, (222)
"We had an amazing family reunion at one of Matt Caudill's properties on Geneva-on-the-Lake. Matt was incredibly accommodating, ensuring all our needs were met. The location of the property was perfect—close to restaurants, entertainment, and everything we needed for a fun and relaxing stay. The home itself was exceptionally well-stocked, making our stay comfortable and hassle-free. Overall, we had a wonderful experience and would highly recommend Matt's property to anyone looking for a great...
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C
Property grounds

Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C

9.4 out of 10, Exceptional, (295)
"This was the perfect landing spot for our fall wine weekend to NE Ohio. We had a great time and would recommend. "
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.