Holiday Homes in Milford

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Featured Holiday Homes in Milford

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (132)
"We just got back from a really great weekend! The rental house was the cutest farmhouse and was decorated so so nicely. It’s so warm and inviting! Dixie, the dog that lives on the property was our absolute favorite. The house is located on a farm and it was fun to watch the farm animals and it was such a beautiful setting. All of the beds were super comfortable and the house was nicely stocked with the necessities. The owners were super responsive and helpful and made sure that our stay was top...
Charming farmhouse in peaceful countryside

Lakefront Syracuse Home w/ Deck & Private Dock!

9.8 out of 10, Exceptional, (8)
"In town for a wedding and it was the perfect location. "
Lakefront Syracuse Home w/ Deck & Private Dock!

Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath

10.0 out of 10, Exceptional, (38)
"The cottage was perfect for us. It was very clean, fully equipped and the views were amazing. A big thank you to Lois and Todd for their kindness."
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath

Eagle's View Indiana waterfront home on a premier fishing lake pontoon included!

10.0 out of 10, Exceptional, (14)
"Awesome recharge for my husband and I!"
Eagle's View Indiana waterfront home on a premier fishing lake pontoon included!

| Hot Tub | Amish Farm Country | Pergola | Deck |

10.0 out of 10, Exceptional, (74)
"Great property, clean, comfortable, close to town and activities "
The price is AU$405
includes taxes & fees
4 Dec - 5 Dec
| Hot Tub | Amish Farm Country | Pergola | Deck |

Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL

9.6 out of 10, Exceptional, (20)
"Great place. We had an amazing weekend and would use this house again! "
Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL

Waters Edge Cottage on Big Barbee Lake!

10.0 out of 10, Exceptional, (16)
"Overall our stay was great! The VRBO and property are both really small, but we knew that from the listing. The kitchen is stocked with basic necessities and a few extras, but it is difficult to find what you’re looking for. I did not find the washer and dryer right away so we ended up not using it but it does tell you where it’s located if you read more carefully the check in info."
Waters Edge Cottage on Big Barbee Lake!

Spacious FiveStar Lakefront Retreat-4BR/4BA w/HotTub,GameRoom, FirePit, SUP

8.8 out of 10, Excellent, (19)
"Very clean spacious Great Lake house. Would stay here again. "
The price is AU$990
includes taxes & fees
1 Dec - 2 Dec
Spacious FiveStar Lakefront Retreat-4BR/4BA w/HotTub,GameRoom, FirePit, SUP

Beautiful Private Setting !!!

10.0 out of 10, Exceptional, (13)
"It was perfect for our needs and the dog was happy he could play with his frisbee "
The price is AU$692
includes taxes & fees
1 Dec - 2 Dec
Beautiful Private Setting !!!

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

10.0 out of 10, Exceptional, (45)
"The house was beautiful! Very comfortable and welcoming. Will definitely stay here again if in the area!"
The price is AU$383
includes taxes & fees
23 Dec - 24 Dec
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres

9.4 out of 10, Exceptional, (23)
"Great cottage, outside of city life. Absolutely adorable dog on property to greet you coming and going. Nice set-up, everything we needed. GPS takes you past the cottage to another farm nearby; be careful if traveling in the dark. "
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres

Primitive Goshen Pine Lodge with Fireplace!

9.0 out of 10, Wonderful, (7)
"spent most of the time away from house but did play some yard games"
Primitive Goshen Pine Lodge with Fireplace!

Adorable Wawasee Cottage in Oakwood Park

10.0 out of 10, Exceptional, (8)
"Enjoyed our stay/would stay again."
The price is AU$561
includes taxes & fees
1 Dec - 2 Dec
Adorable Wawasee Cottage in Oakwood Park

Beautiful Lake Home in a quiet relaxing setting. Access to paddle boats.

9.8 out of 10, Exceptional, (61)
"We rented this beautiful, spacious home for the weekend to celebrate my sister’s birthday. There were twelve adults and we had plenty of room. We were pleasantly surprised to see that everything was supplied including paper towels, dish washing detergent, and showers essentials. "
Beautiful Lake Home in a quiet relaxing setting. Access to paddle boats.

Kountry Lane Stables | Horse Farm w/ HOT TUB + Fire Pit!

10.0 out of 10, Exceptional, (8)
"Great place for a getaway with family & friends. Interior of the house was very clean. The exterior could use some TLC. Everyone enjoyed the stay. Definitely would consider staying again."
Kountry Lane Stables | Horse Farm w/ HOT TUB + Fire Pit!

Charming 3-bedroom lake house on Tri lakes 6 miles north of Columbia City.

9.4 out of 10, Exceptional, (6)
"Very clean, nice lake cottage with great view of Shriner Lake to the front and Cedar Lake to the back. We did and early “Thanksgiving “ at the Lake and it was fine. Could use a few more glasses, plates and utensils … service for 4 was all I found and parking is limited 2 to cars but we brought disposable plates cups utensils. Netflix and wifi and 2 separate bunk rooms. Worked for us. We had a good time and owner very nice and communicated. Thanks!"
Charming 3-bedroom lake house on Tri lakes 6 miles north of Columbia City.

Trail Side in the Heart of Winona Lake

10.0 out of 10, Exceptional, (14)
"Last minute getaway to the beautiful fall foliage. Couldn’t have asked for a better area or Accommodations to stay in."
The price is AU$390
includes taxes & fees
20 Dec - 21 Dec
Trail Side in the Heart of Winona Lake

3BD Modern Home w/ fire pit: DT (30 Mins ND)

10.0 out of 10, Exceptional, (1)
"Clean and comfortable home with many thoughtful amenities! Very friendly and responsive host. Quick Uber/Lyft drive away from Notre Dame stadium. No complaints! Will book again during our next trip and highly recommended if staying in the South Bend area. "
The price is AU$673
includes taxes & fees
1 Dec - 2 Dec
3BD Modern Home w/ fire pit: DT (30 Mins ND)

Charming Middlebury Retreat w/ Patio & Fire Pit

2.0 star property
10.0 out of 10, Exceptional, (1)
"."
Charming Middlebury Retreat w/ Patio & Fire Pit

Barbee Lake Big House! Sleeps 14+ Game Garage! Pier and Dock to Barbee!

9.6 out of 10, Exceptional, (5)
"Worked for the ten of us comfortably. Would absolutely book again"
Barbee Lake Big House! Sleeps 14+ Game Garage! Pier and Dock to Barbee!
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 Milford

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

10.0 out of 10, Exceptional, (21)
"I loved this vrbo stay! So clean and nice. "
The price is AU$597
includes taxes & fees
2 Dec - 3 Dec
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (132)
"We just got back from a really great weekend! The rental house was the cutest farmhouse and was decorated so so nicely. It’s so warm and inviting! Dixie, the dog that lives on the property was our absolute favorite. The house is located on a farm and it was fun to watch the farm animals and it was such a beautiful setting. All of the beds were super comfortable and the house was nicely stocked with the necessities. The owners were super responsive and helpful and made sure that our stay was top...
Charming farmhouse in peaceful countryside

Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath

10.0 out of 10, Exceptional, (38)
"The cottage was perfect for us. It was very clean, fully equipped and the views were amazing. A big thank you to Lois and Todd for their kindness."
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.