Holiday Homes in Orland

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Orland

Recently renovated country cottage, 2.5 miles from Shipshewana
10.0 out of 10, Exceptional, (210)
"Wanting to get away to celebrate our 33rd anniversary. Had a wonderful time in the area. The house was great, it was quiet and had a nice sunrise in the morning. Good location close to shopping and eating."
The price is AU$278
includes taxes & fees
29 Sept - 30 Sept
Recently renovated country cottage, 2.5 miles from Shipshewana
Cozy Home Retreat
2.0 star property
10.0 out of 10, Exceptional, (4)
"This cute ranch is very clean and well stocked for guests. We only had three people in our group, but the house can definitely host more people comfortably. It is very close to downtown Shipshewana and other surrounding shops and attractions. My only suggestion would possibly be investing in new mattresses. Although we slept comfortably, the quality could be improved. The owner was responsive to my messages in a timely manner. Instructions for the home were clear and easy to follow. We would...
The price is AU$574
includes taxes & fees
30 Sept - 1 Oct
Cozy Home Retreat
Newly Remodeled Cabin Steps from Sylvan Lake
10.0 out of 10, Exceptional, (29)
"This is the second time we have rented this sweet cottage for a long summer weekend. Property is very clean and is convenient to beach, grocery and is just steps from the lake. Beautiful views, quiet neighborhood. "
Newly Remodeled Cabin Steps from Sylvan Lake
Rest, Relax and Reboot...pet friendly
9.6 out of 10, Exceptional, (113)
"We had a wonderful time here! Such a quiet and peaceful setting. We booked this property specifically to watch the Perseid meteor shower, and were treated to so much more! We were lucky enough to see the Norther Lights over the lake too! Had a great time taking the pontoon around the lake, and grilling on the quaint back porch. Being able to have our dog with was awesome as well! "
Rest, Relax and Reboot...pet friendly
Shipshewana Guest House with Fire Pit!
10.0 out of 10, Exceptional, (26)
"Highly recommended."
Shipshewana Guest House with Fire Pit!
Songbird Haven, 3 min from town, full house, 3 bedrooms, 5 bed, 2 bathrooms,
9.8 out of 10, Exceptional, (10)
"We stayed in this lovely home for 2 nights so we could go to a few concerts at the Blue Gate. The home was everything I hoped it would be. It was as warm and welcoming as Miriam is and in a beautiful, quiet neighborhood. I would definitely stay here again in the future. "
Songbird Haven, 3 min from town, full house, 3 bedrooms, 5 bed, 2 bathrooms,
Charming Reading Getaway w/ Private Dock!
2.0 star property
9.4 out of 10, Exceptional, (3)
"Great spot! A clean and well appointed property with all the necessary amenities of home. Solid WiFi for staying connected. And really comfy beds and super clean bathrooms and kitchen. Nice view of the water, but be cautious of neighbors who will let you know if you accidentally step foot on their property. They don’t seem to take kindly to strangers. Host was super responsive with questions and very helpful! All in all a nice spot if you find yourself with a reason to visit Reading....
Charming Reading Getaway w/ Private Dock!
Kayaks | Relax by River | 10 Min to Shipshewana |
10.0 out of 10, Exceptional, (5)
"It was very nice house as described on VRBO. It was very peaceful and definitely got to see lot of birds on the neighbors feeders and fish jumping in the water. But the gas grill was left a mess with the previous stays used foil on the grill and bees flying inside of it and looked like they tried burning a bucket and the aluminium foil in the fire pit. "
The price is AU$284
includes taxes & fees
19 Sept - 20 Sept
Kayaks | Relax by River | 10 Min to Shipshewana |
Emma's Place
10.0 out of 10, Exceptional, (34)
"Very accommodating "
The price is AU$470
includes taxes & fees
19 Sept - 20 Sept
Emma's Place
Paradise - Coldwater/North Lake Rental - Monthly/Weekly /4 day off season
9.8 out of 10, Exceptional, (86)
"This house was the perfect place for my freinds and I to have a girls weekend. We each had our own beds and only 2 people shared a room. The deck is absolutely amazing. We spent 2 full days drinking coffee and crafting all day. I could not have imagine a better weekend and house for our annual girls trip. The memories made will be charished for a lifetime."
Paradise - Coldwater/North Lake Rental - Monthly/Weekly /4 day off season
Secluded Riverside Log Home in Southern Michigan
10.0 out of 10, Exceptional, (73)
"Great location, great host, definitely would come back. "
Secluded Riverside Log Home in Southern Michigan
Beautiful Lake home on Morrison Lake; Coldwaters North Chain of Lakes.
10.0 out of 10, Exceptional, (92)
"Very nice house. Could use a little TLC and cleaning up outside."
Beautiful Lake home on Morrison Lake; Coldwaters North Chain of Lakes.
Lakefront house on All Sport Palmer Lake with pier to dock your boat/kayak.
9.8 out of 10, Exceptional, (20)
"Great little house on Palmer Lake, we had enjoyed the little town and activities on the lake! Perfect for a family!"
Lakefront house on All Sport Palmer Lake with pier to dock your boat/kayak.
LAKE HOUSE LUXURY WITH PANORAMIC VIEWS OF THE WATERFRONT 300FT DOCK
9.4 out of 10, Exceptional, (11)
"Everything was to our expectations. Nice house . "
LAKE HOUSE LUXURY WITH PANORAMIC VIEWS OF THE WATERFRONT 300FT DOCK
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
Lake Retreat With Hot Tub
10.0 out of 10, Exceptional, (1)
"Stayed here for my daughters 17th birthday. It was perfect. The view was great, hot tub was a hit and the space was cozy. The bed in the single queen room was uncomfortable to me but it would not deter me from booking again!"
The price is AU$395
includes taxes & fees
29 Sept - 30 Sept
Lake Retreat With Hot Tub
Full House on the Lake with Free kayaks, paddleboats and a fishing boat.
9.6 out of 10, Exceptional, (67)
"This was a great place to stay! Beautiful sunsets, quite setting, access to water toys was great to get out on the lake. My son caught a bunch of crappie. It is remote however your very close to town. I would recommend it as place to stay. Had everything you would need. "
The price is AU$409
includes taxes & fees
1 Oct - 2 Oct
Full House on the Lake with Free kayaks, paddleboats and a fishing boat.
Davis Street Shipshewana
10.0 out of 10, Exceptional, (59)
"We loved our stay here. The location is perfect. The house was perfect for us 4 adults. The owner supplied us with everything we needed plus more. The owner was great to work with. We have absolutely no complaints and we hope to stay there again. "
The price is AU$307
includes taxes & fees
29 Sept - 30 Sept
Davis Street Shipshewana
Lake cottage with a great view 20 minutes from Shipshewana.
10.0 out of 10, Exceptional, (85)
"Thank you for making our stay so enjoyable! Beautiful view of lake and the cottage had everything we needed. The deck was so nice for meals and relaxing. The home was very comfortable and well maintained with beautiful gardens. Kids were able to swim from pier….loved the games and puzzles and nice fire pit for S’mores! The lake is quiet and several sandy areas to anchor and swim. The cottage was perfect for us and hope to return. "
Lake cottage with a great view 20 minutes from Shipshewana.
Lakefront home on All-Sports Long Lake
10.0 out of 10, Exceptional, (96)
"This was our second time staying at this home. We totally enjoyed our stay and would love to come back. The owners thought of everything we would need the communication with Laura was great!"
Lakefront home on All-Sports Long Lake
Don't see what you're looking for?
See all available properties in Orland
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.
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Orland

Recently renovated country cottage, 2.5 miles from Shipshewana
10.0 out of 10, Exceptional, (210)
"Wanting to get away to celebrate our 33rd anniversary. Had a wonderful time in the area. The house was great, it was quiet and had a nice sunrise in the morning. Good location close to shopping and eating."
The price is AU$278
includes taxes & fees
29 Sept - 30 Sept
Recently renovated country cottage, 2.5 miles from Shipshewana
Rest, Relax and Reboot...pet friendly
9.6 out of 10, Exceptional, (113)
"We had a wonderful time here! Such a quiet and peaceful setting. We booked this property specifically to watch the Perseid meteor shower, and were treated to so much more! We were lucky enough to see the Norther Lights over the lake too! Had a great time taking the pontoon around the lake, and grilling on the quaint back porch. Being able to have our dog with was awesome as well! "
Rest, Relax and Reboot...pet friendly
NEW LISTING! Luxury Lakefront Home on Lake James
10.0 out of 10, Exceptional, (45)
"Handled 16 family members easily. Nice dock and swimming area. Kids had great time in lake and bunk room. Comfortable beds. Sandbar on lake was fun. Park nearby worth a visit. Fun trip!"
NEW LISTING! Luxury Lakefront Home on Lake James
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.