Orland Vacation Rentals

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Browse Select Orland Vacation Homes

Full House on the Lake with Free kayaks, paddleboats and a fishing boat.

9.6 out of 10, Exceptional, (73)
"Nice place to get away for a long weekend. "
The price is CA $214
CA $273 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Full House on the Lake with Free kayaks, paddleboats and a fishing boat.

Davis Street Shipshewana

10.0 out of 10, Exceptional, (63)
"Comfortable "
The price is CA $158
CA $293 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Davis Street Shipshewana

Lakefront Home on Crooked Lake, Beautiful Views and Plenty of Space and Hot Tub!

9.8 out of 10, Exceptional, (35)
" Hard to watch baseball playoffs when Tv is streaming.Wi-Fi was going in and out. Grandkids brought fishing poles to fish off dock and it was brought in already. Owner said it’s usually out till end of October. Hot tub was not ready for first night there, we had to turn up heat and wait till next day. Place was clean and had plenty of room. Lots of towels and rags. First VRBO that I had to make beds "
Lakefront Home on Crooked Lake, Beautiful Views and Plenty of Space and Hot Tub!

Songbird Haven, 3 min from town, full house, 3 bedrooms, 5 bed, 2 bathrooms,

10.0 out of 10, Exceptional, (17)
"Mike and Rose thought of everything! The house is gorgeous, the location is great, and our stay was just perfect. Rose responded immediately to any questions I had. We'll certainly rent this wonderful property again."
The price is CA $228
CA $445 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Songbird Haven, 3 min from town, full house, 3 bedrooms, 5 bed, 2 bathrooms,

Destination lake, Million dollar house, million-dollar views

10.0 out of 10, Exceptional, (7)
"We had a couple small families from all over the US and we all had so much fun! Plenty of room for he kiddos and the place had a lot to offer! Will definitely come back again! "
Destination lake, Million dollar house, million-dollar views

The Maple & Oak - Lakefront Home with Private Beach

10.0 out of 10, Exceptional, (4)
"We had a beautiful and relaxing getaway from day to day life. Welcomed change of pace and we both enjoyed the private beach area. "
The Maple & Oak - Lakefront Home with Private Beach

Beautiful Lake house with private sandy beach, hot tub, kayaks, 4 bed, 4 bath

2.0 star property
Beautiful Lake house with private sandy beach, hot tub, kayaks, 4 bed, 4 bath

Lake Retreat With Hot Tub

9.8 out of 10, Exceptional, (6)
"What a cute little place! Perfect for our family and dog. It looks out at the beautiful lake and comes with all sorts of extras like kayaks and bikes. We stayed in the winter so we didn't take advantage of any of the water items but we did make a campfire and s'mores (ingredients provided at house). We also chilled in the hot tub. We had the most relaxing time! The location of this property is great - a few.minutes from stores for groceries, the amish town of Shipshewana and a short drive from...
The price is CA $188
CA $243 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Lake Retreat With Hot Tub

Rest, Relax and Reboot...pet friendly

9.6 out of 10, Exceptional, (118)
"Very nice clean cottage with beautiful views. It was chilly and windy so we didn't take out the boats or kayaks so I guess we will have to come back. Rhonda stopped by to make we got checked in okay and didn't need anything. We thought that was above and beyond and it was appreciated. "
Rest, Relax and Reboot...pet friendly

5 Bedroom Lake Access House and Entertainment Bldg for Rent

9.6 out of 10, Exceptional, (133)
"Great place in an area with several good golfing options. The house has all the amenities that you would want for a several night stay; a lot of space, big back yard, fire pit. Grills to cook, full kitchen and several close restaurants nearby."
5 Bedroom Lake Access House and Entertainment Bldg for Rent

NEW LISTING! Luxury Lakefront Home on Lake James

10.0 out of 10, Exceptional, (48)
"Spent a long weekend at the Lake House - a group of people in town for Trine Homecoming...house was fantastic! Great for entertaining and large groups."
NEW LISTING! Luxury Lakefront Home on Lake James

Secluded Riverside Log Home in Southern Michigan

10.0 out of 10, Exceptional, (74)
"It was supposed to be a gathering of siblings and spouses each traveling from a couple hours away. A getaway for seven turned into a fun weekend for four. One missed because of illness. Two missed because of a family death the day we were supposed to stay. Owners were very sympathetic and understanding of the situation. The four who stayed had a good time and we hope to book again for a more complete siblings weekend."
Secluded Riverside Log Home in Southern Michigan

Lakefront home on All-Sports Long Lake

10.0 out of 10, Exceptional, (102)
"We enjoyed our stay over the Thanksgiving weekend!! "
Lakefront home on All-Sports Long Lake

Sturgis Home w/ Yard < 1 Mi to Minnewaukan Lake

10.0 out of 10, Exceptional, (11)
"We really enjoyed our stay. The home was kept up nicely and very clean. It was so nice to be able to park in the garage. The view to the private back yard was wonderful. There were several small comforts and conveniences that we enjoyed such as water bottles in the refrigerator, keurig coffee, and microwave popcorn. The only thing that we had any issue with was that the satellite dish TV was not very user friendly. We couldn't figure out how to watch what we wanted to. Fortunately, we were able...
Sturgis Home w/ Yard < 1 Mi to Minnewaukan Lake

Come enjoy this absolute dream for a family vacation or a getaway with friends!

9.8 out of 10, Exceptional, (6)
"Derek was a great host and the property was just as described, appreciated the Christmas 🎄 "
Come enjoy this absolute dream for a family vacation or a getaway with friends!

Hamilton Haven Cottage

10.0 out of 10, Exceptional, (3)
"Super clean and tastefully decorated newly remodeled lake cottage. Very friendly and caring host. The town of Hamilton is the perfect small town slowdown getaway on a picturesque lake."
Hamilton Haven Cottage

Spacious House + boat house on clear, sandy-bottom lake. Arcade + Billiards room

10.0 out of 10, Exceptional, (2)
"Perfect getaway for my book club anniversary weekend. Everything was pretty much as stated. Only thing was one of the bedrooms wasn't really a bedroom. There were plenty of beds so we made due. We would consider staying again. in warmer months. "
Spacious House + boat house on clear, sandy-bottom lake. Arcade + Billiards room

Family-Friendly Retreat on Long Noble Lake!

10.0 out of 10, Exceptional, (9)
"Annual get together. Brothers and nephews"
Family-Friendly Retreat on Long Noble Lake!

Recently renovated country cottage, 2.5 miles from Shipshewana

10.0 out of 10, Exceptional, (225)
"We loved our stay. The house was immaculate. And it was exactly as described. Was perfect for a night away with friends as went to a concert in Shipshewana. We would absolutely stay again."
The price is CA $194
CA $286 total
includes taxes & fees
Dec 27 - Dec 28
Recently renovated country cottage, 2.5 miles from Shipshewana

Emma's Place

10.0 out of 10, Exceptional, (37)
"We stayed one night and were very comfortable. The house was very clean and easy to find. "
The price is CA $215
CA $449 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Emma's Place
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 Orland

Full House on the Lake with Free kayaks, paddleboats and a fishing boat.

9.6 out of 10, Exceptional, (73)
"Nice place to get away for a long weekend. "
The price is CA $214
CA $273 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Full House on the Lake with Free kayaks, paddleboats and a fishing boat.

Davis Street Shipshewana

10.0 out of 10, Exceptional, (63)
"Comfortable "
The price is CA $158
CA $293 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Davis Street Shipshewana

Rest, Relax and Reboot...pet friendly

9.6 out of 10, Exceptional, (118)
"Very nice clean cottage with beautiful views. It was chilly and windy so we didn't take out the boats or kayaks so I guess we will have to come back. Rhonda stopped by to make we got checked in okay and didn't need anything. We thought that was above and beyond and it was appreciated. "
Rest, Relax and Reboot...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.