Photo by Eric O

Madison Holiday Rentals

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Holiday Rentals in Madison

Lakefront home just minutes from wineries. Backyard sunsets!

9.6 out of 10, Exceptional, (20)
"Enjoyed the stay with family. The set up was great for all with the games( Golden Tee, Skeeball, darts, PacMan, etc.). My wife did not enjoy the “midges” (flys) but the sound of the water made up for it! Would recommend to all!"
Lakefront home just minutes from wineries. Backyard sunsets!

Lakefront Property, Family Friendly and Pets Allowed

9.8 out of 10, Exceptional, (102)
"The House was very clean and the view of the the lake was outstanding!! The bedrooms were a nice size and beds comfortable! The jacuzzi tub was wonderful and the hot tub was really nice as well. I understand now why this property is always booked!! I will be looking to rebook hopefully next summer since there currently are no openings we highly recommend this rental property!!!"
Lakefront Property, Family Friendly and Pets Allowed

Secluded Hot Tub Retreat by Ohio Wine Trail & Lake

10.0 out of 10, Exceptional, (7)
"We decided to take a nearby winter getaway and searched VRBO for a home with a hot tub which was pet friendly. This home near Geneva-on-the-Lake fit the criteria and was perfect for our needs. We were 2 couples and the layout with 2 bedrooms/1 bath near front of house with another bedroom/bath in back of house was the perfect separation. A winter storm came in as we arrived and it was below freezing for our 4 nights but we still used the hot tub 2 of the evenings.We definitely enjoyed our time...
The price is AU$845
includes taxes & fees
13 Feb - 14 Feb
Secluded Hot Tub Retreat by Ohio Wine Trail & Lake

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

9.4 out of 10, Exceptional, (231)
"Took a trip with family and friends for my birthday. Location was perfect. Best part of this location was that everyone was able to have their own room. "
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries

LAKEFRONT LOFT-PERFECT COUPLES GETAWAY Rent 2 /3rd free until May 22--ask!

10.0 out of 10, Exceptional, (318)
"A Host was incredible!"
The price is AU$256
includes taxes & fees
16 Feb - 17 Feb
LAKEFRONT LOFT-PERFECT COUPLES GETAWAY Rent 2 /3rd free until May 22--ask!

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

9.4 out of 10, Exceptional, (299)
"This was our second time staying at this property. Once again it was a great time. The house is super clean and comfortable. Matt is always responsive to my questions. We would definitely stay here again. "
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C

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

9.8 out of 10, Exceptional, (182)
"We had a great time! We had 8 adults and 6 kiddos and we had plenty of room! We had plenty of everything we needed. There is a regular drip coffee pot and one for k-cups. Many of the shops and restaurants in GOTL are closed in the winter. We would love to see how the city transforms in the summer! "
Great Strip Location | Lake View | Pet Friendly | A/C | Sauna| Wine Country|WiFi

3Cottages on Strip, Lakefront, AC, WiFi, Fire pit, Deck over Lake, Pet Friendly

9.6 out of 10, Exceptional, (109)
"I stayed at this property with my family over a weekend in October and it was awesome. Here are some things we loved about the property: - Space: the cabins sit on a plot of land overlooking the lake. There's plenty of space for cars (we had 5) and for recreation. We set up corn hole, games for the kids, etc. and had ample room to play. There's a nice patio between two cabins where we spent a lot of time. We grilled out, sat by the fire pit in the evening and, in general, enjoyed being outside....
3Cottages on Strip, Lakefront, AC, WiFi, Fire pit, Deck over Lake, Pet Friendly

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

9.4 out of 10, Exceptional, (224)
"House was great. Lots of room. Was perfect for adults, not too many bunk beds or single beds, that adults do not want to sleep in. Close to strip and easy drive to most of the wineries. Perfect for large group we had 11 adults and still had extra rooms. Has everything you could need!"
Center of Strip |Pet Friendly|A/C|Wi-fi & Cable|Stately Home|Steps from Winery

Glamorous Camping - Hot Tub - GOTL - Sunset Vacation Rentals

9.6 out of 10, Exceptional, (63)
"This was our 2nd time here.. Bed is comfy and the hot tub us great. is great. "
Glamorous Camping - Hot Tub - GOTL - Sunset Vacation Rentals

Great Strip Location | Walk to Lake|Wine Country|A/C|Fireplace|Family Friendly

9.6 out of 10, Exceptional, (93)
"Our go to place the last 3 years when visiting family at Christmas. Great location, clean, comfortable with plenty of room. Looking forward to stay there in the summer. "
Great Strip Location | Walk to Lake|Wine Country|A/C|Fireplace|Family Friendly

beautiful newly remodeled cottage - Walk to strip close to spire

10.0 out of 10, Exceptional, (70)
" We stayed at this charming property in Geneva-on-the-Lake during the winter, and it was nothing short of magical. The house was warm, inviting, and perfect for cozying up after a day of exploring. From the crackling fireplace to the comfy furniture, it felt like a home away from home. Even in the off-season, there was so much to enjoy. The snow-covered lake was breathtaking, and we loved walking along the quiet streets, enjoying the peacefulness of the area. Local wineries and restaurants were...
The price is AU$302
includes taxes & fees
18 Feb - 19 Feb
beautiful newly remodeled cottage - Walk to strip close to spire

Main Strip Location | Pet Friendly | Wi-Fi & Cable | A/C | Steps from Winery

9.6 out of 10, Exceptional, (229)
"Exactly as pictured,had everything we needed right down to the fire extinguisher. "
Main Strip Location | Pet Friendly | Wi-Fi & Cable | A/C | Steps from Winery

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

9.4 out of 10, Exceptional, (80)
"We stayed in the four bedroom cottage clean the arm and wonderful. Loved the ping pong table Thank you Matt "
Great Strip Location|WalktoLake|Wine Country|AC|Grill&Firepit|FamilyFriendly

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

9.4 out of 10, Exceptional, (68)
"We are from Conneaut, but had a lot of business to take of in Mentor. My husband also needed to be able to get back to Conneaut as needed for other work projects. Instead of driving back and forth between the two we decided to get a place in Geneva.It worked out GREAT! It was so convenient and the cottage was clean, comfortable, pet friendly & well appointed with a perfect location. Lots of restaurants nearby and easy access to route 84. Matt is terrific!!!We'll be back - we highly...
East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly

Lakefront - Winery - GOTL Oasis- Sunset Vacation Rentals

9.4 out of 10, Exceptional, (51)
"Beautiful views of the lake and all the stacking ice was amazing ! Over all a great stay. Only issues was dog hair left by a previous guest and a patio door wouldn’t lock. Would love to come back in the summer. "
Lakefront - Winery - GOTL Oasis- Sunset Vacation Rentals

Cozy cabin with views of Lake Erie and colorful sunsets!

10.0 out of 10, Exceptional, (50)
"Had a great stay. Was out here working"
The price is AU$364
includes taxes & fees
17 Feb - 18 Feb
Cozy cabin with views of Lake Erie and colorful sunsets!

Cozy cottage with Lake Erie access

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a great time! The cottage was comfortable and had everything we needed for our holiday visit.Great space for a family, or a couples retreat.I would highly recommend this cottage, and would rent again in the future"
The price is AU$390
includes taxes & fees
24 Feb - 25 Feb
Cozy cottage with Lake Erie access

DewDrop Cottage: Walk to the strip! 2 bed 1 bath, sleeps 5

10.0 out of 10, Exceptional, (190)
"Very cozy."
DewDrop Cottage: Walk to the strip! 2 bed 1 bath, sleeps 5

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

9.8 out of 10, Exceptional, (48)
"The place we was in was very nice. It was very clean and relaxing. The property was very clean. Everything worked very well. It was super close to Everything we wanted to do. Overall the location and the place was 10/10. The only negative thing i have to say that the front door blind was broken when we arrivedwe got there is that"
Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly
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 types of properties in Madison you may be interested in

Holiday Inn Express & Suites Madison by IHG

2.5 star property
9.4 out of 10, Exceptional, (520)
"Nice"
The price is AU$177
includes taxes & fees
2 Mar - 3 Mar
Holiday Inn Express & Suites Madison by IHG

Hampton Inn Madison

2.5 star property
9.6 out of 10, Exceptional, (661)
"The check in person was friendly . A great way to start the visit "
The price is AU$193
includes taxes & fees
2 Mar - 3 Mar
Hampton Inn Madison

Lakefront Property, Family Friendly and Pets Allowed

9.8 out of 10, Exceptional, (102)
"The House was very clean and the view of the the lake was outstanding!! The bedrooms were a nice size and beds comfortable! The jacuzzi tub was wonderful and the hot tub was really nice as well. I understand now why this property is always booked!! I will be looking to rebook hopefully next summer since there currently are no openings we highly recommend this rental property!!!"
Lakefront Property, Family Friendly and Pets Allowed
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.

Frequently asked questions

Can I find a holiday rental in Madison?

Yes, there are holiday rentals close to the most popular sights in Madison, or you can select a more secluded option if you're looking for a relaxing stay. Madison is known for its wineries and theatres. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best holiday rentals that Madison has to offer?

Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries: This holiday home rental outside of Madison is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals will I find in Madison?

With 23 Expedia holiday rentals, you're guaranteed to find just the right place for your Madison stay.

What can I see and do in Madison?

Lake Erie and Hogback Ridge are a couple of scenic spots to enjoy the outdoors, whereas Rabbit Run Community Arts Association is one of the cultural attractions. While here, Laurentia Vineyard & Winery and Chalet Debonne Vineyards are other places worth a visit.

What are holiday rentals like in Madison?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Madison. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family trips.