Orland Holiday Rentals

  • 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

Holiday Rentals 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 AU$308
includes taxes & fees
2 Jan - 3 Jan 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 AU$330
includes taxes & fees
5 Jan - 6 Jan 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

Relax by the lake- enjoy wine country and ski slopes

9.0 out of 10, Wonderful, (9)
"This Host! When my head was spinning from the tragic loss of my Father—she was direct and kind! Completely understanding of the needs of our family! This Is a beautiful property; fully stocked well taken care of and very clean! I can’t thank you enough, France, for making our stay as low stress possible! 💯% recommend checking this place out💕"
The price is AU$1,332
includes taxes & fees
26 Dec - 27 Dec
Relax by the lake- enjoy wine country and ski slopes

Serene Lake/Fishing Retreat w/outdoor hot tub and indoor Jaccuzzi

9.8 out of 10, Exceptional, (82)
"It was hard to tear myself away. Absolutely wonderful. Perfect for a couple!"
The price is AU$367
includes taxes & fees
1 Jan - 2 Jan 2025
Serene Lake/Fishing Retreat w/outdoor hot tub and indoor Jaccuzzi

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!

Live & Love Life on the Lake!

9.6 out of 10, Exceptional, (37)
"We were only there during the night and gone before the sun came up but it was a nice place to stay and will try to book again when we come back "
The price is AU$394
includes taxes & fees
26 Dec - 27 Dec
Live & Love Life on the Lake!

Cozy ‘Haven of Rest’ Home w/ Amish Country Views!

10.0 out of 10, Exceptional, (49)
"What an awesome experience we had! Loved the stay and would highly recommend!! Jackie was so nice and made sure we had everything we needed!!😊"
Cozy ‘Haven of Rest’ Home w/ Amish Country Views!

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

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 AU$319
includes taxes & fees
31 Dec - 1 Jan 2025
Recently renovated country cottage, 2.5 miles from Shipshewana

Escape on Long Lake a waterfront Log Cabin

10.0 out of 10, Exceptional, (35)
"The house was very nice, with a great deck overlooking the lake. We liked having our boat at the dock, with launch site just down the street. We would definitely stay here again."
Escape on Long Lake a waterfront Log Cabin

Indian Lakes Cabin with private beach and dock lake side

9.6 out of 10, Exceptional, (74)
"Rustic cabin located on a beautiful lake. We had a great time with no issues. "
Indian Lakes Cabin with private beach and dock lake side

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

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

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!

Three Swans Lakehouse: Thanksgiving Lakefront Getaway!

9.2 out of 10, Wonderful, (25)
"Perfect place for a quiet getaway. This property was the cleanest house I have ever rented from in the past. They had every amenity you could think of. We would love to stay there again in the future and enjoy the peacefulness of the area. "
Three Swans Lakehouse: Thanksgiving Lakefront Getaway!

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 AU$504
includes taxes & fees
30 Dec - 31 Dec
Emma's Place

Paradise - Coldwater/North Lake Rental - Monthly/Weekly /4 day off season

10.0 out of 10, Exceptional, (93)
"Great place to stay. "
Paradise - Coldwater/North Lake Rental - Monthly/Weekly /4 day off season

Hillsdale County, Michigan: weddings, groups, Hillsdale College, Trine Univ.

10.0 out of 10, Exceptional, (62)
"Nick and Marisa provided a beautiful home for us. The accommodations and their graciousness exceeded our expectations. Thank you!"
Hillsdale County, Michigan: weddings, groups, Hillsdale College, Trine Univ.

LAKE FRONT COTTAGE ON IYOPAWA ISLAND GOLF COURSE

9.6 out of 10, Exceptional, (39)
"What a great week away from the business of life. Great location: golf course across the street, on the lake for boating, sand bar, fishing, walking around the island, golf carting if you bring one, and great community of friendly people. We had 8 people stay comfortably, 1 restroom is a bit challenging but do able. Parking is a little struggle for day guests. Only 3 parking spots including 1 in the garage. But again all minor details that are over come by the location. Refrigerator/freezer in...
LAKE FRONT COTTAGE ON IYOPAWA ISLAND GOLF COURSE
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.
Don't see what you're looking for?
See all available properties in Orland
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Orland you may be interested in

Van Buren Hotel

2.5 star property
8.8 out of 10, Excellent, (1083)
"Nice hotel…a little farther than what we thought from downtown…staff was friendly and helpful"
The price is AU$166
includes taxes & fees
5 Jan - 6 Jan 2025
Van Buren Hotel

Farmstead Inn & Conference Center

2.5 star property
9.6 out of 10, Exceptional, (1000)
"The stay was awesome. Had a great time there. The meal was so good and sight seeing in the town was great 🆒We’ll go back again!!!"
The price is AU$236
includes taxes & fees
29 Dec - 30 Dec
Farmstead Inn & Conference Center

Blue Gate Garden Inn

2.5 star property
9.6 out of 10, Exceptional, (1247)
"Close to downtown "
The price is AU$198
includes taxes & fees
29 Dec - 30 Dec
Blue Gate Garden Inn
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 Orland?

Yes, there are holiday rentals close to the most popular sights in Orland, or you can select a more secluded option if you're looking for a relaxing stay.

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

Full House on the Lake with Free kayaks, paddleboats and a fishing boat. : This holiday home rental outside of Orland is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, 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 selection of books.

What’s there to see and do in Orland?

While exploring the area, visit family-friendly sights like Adventure Zone, or get outside and enjoy nature at Wall Lake. In the wider area, you’ll find Jimmerson Lake and Pokagon State Park.

What’s a holiday rental in Orland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Orland. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip.